DE2332232A1 - Neues verfahren zur herstellung von imidazo eckige klammer auf 2,1-a eckige klammer zu isoindol-5-onen - Google Patents

Info

Publication number

DE2332232A1

DE2332232A1 DE19732332232 DE2332232A DE2332232A1 DE 2332232 A1 DE2332232 A1 DE 2332232A1 DE 19732332232 DE19732332232 DE 19732332232 DE 2332232 A DE2332232 A DE 2332232A DE 2332232 A1 DE2332232 A1 DE 2332232A1

Authority

DE

Germany

Prior art keywords

water

isoindol

imidazo

ones

formula

Prior art date

1972-06-28

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Pending

Links

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• 238000000034 method Methods 0.000 title claims description 11
• 238000004519 manufacturing process Methods 0.000 title 1
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
• 150000001875 compounds Chemical class 0.000 claims description 12
• 239000011541 reaction mixture Substances 0.000 claims description 8
• SOWOYMBNJVLWGP-UHFFFAOYSA-N isoindol-5-one Chemical class O=C1C=CC2=CN=CC2=C1 SOWOYMBNJVLWGP-UHFFFAOYSA-N 0.000 claims description 5
• 239000000376 reactant Substances 0.000 claims description 5
• 239000001257 hydrogen Substances 0.000 claims description 4
• 229910052739 hydrogen Inorganic materials 0.000 claims description 4
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
• 238000002360 preparation method Methods 0.000 claims description 4
• 238000010992 reflux Methods 0.000 claims description 4
• 229910052801 chlorine Inorganic materials 0.000 claims description 3
• 239000000460 chlorine Substances 0.000 claims description 3
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
• 229910052731 fluorine Inorganic materials 0.000 claims description 2
• 239000011737 fluorine Substances 0.000 claims description 2
• 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 2
• UVNXNSUKKOLFBM-UHFFFAOYSA-N imidazo[2,1-b][1,3,4]thiadiazole Chemical compound N1=CSC2=NC=CN21 UVNXNSUKKOLFBM-UHFFFAOYSA-N 0.000 claims 1
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
• 238000006243 chemical reaction Methods 0.000 description 8
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
• 239000003960 organic solvent Substances 0.000 description 4
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
• 239000012429 reaction media Substances 0.000 description 3
• YWECCEXWKFHHQJ-UHFFFAOYSA-N 2-(4-chlorobenzoyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=C(Cl)C=C1 YWECCEXWKFHHQJ-UHFFFAOYSA-N 0.000 description 2
• 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
• DSMHZQNWQRXKKJ-UHFFFAOYSA-N imidazo[1,2-b]isoindol-5-one Chemical class C1=CC=C2C3=NC=CN3C(=O)C2=C1 DSMHZQNWQRXKKJ-UHFFFAOYSA-N 0.000 description 2
• 230000035484 reaction time Effects 0.000 description 2
• ASSUNYJRBMKLBJ-UHFFFAOYSA-N 2-(3,4-dichlorobenzoyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=C(Cl)C(Cl)=C1 ASSUNYJRBMKLBJ-UHFFFAOYSA-N 0.000 description 1
• FSMXJLAATHSRCB-UHFFFAOYSA-N 2-(3-chlorobenzoyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=CC(Cl)=C1 FSMXJLAATHSRCB-UHFFFAOYSA-N 0.000 description 1
• QEJCZBRESAWPCT-UHFFFAOYSA-N 2-(3-fluorobenzoyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=CC(F)=C1 QEJCZBRESAWPCT-UHFFFAOYSA-N 0.000 description 1
• FJAZVXUPZQSZKI-UHFFFAOYSA-N 2-(4-fluorobenzoyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=C(F)C=C1 FJAZVXUPZQSZKI-UHFFFAOYSA-N 0.000 description 1
• FGTYTUFKXYPTML-UHFFFAOYSA-N 2-benzoylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 FGTYTUFKXYPTML-UHFFFAOYSA-N 0.000 description 1
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 1
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
• WUFFYAFXNGRHNO-UHFFFAOYSA-N 9b-(4-chlorophenyl)-2,3-dihydro-1h-imidazo[2,1-a]isoindol-5-one Chemical compound C1=CC(Cl)=CC=C1C1(C2=CC=CC=C2C2=O)N2CCN1 WUFFYAFXNGRHNO-UHFFFAOYSA-N 0.000 description 1
• PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
• 230000000578 anorexic effect Effects 0.000 description 1
• 238000010533 azeotropic distillation Methods 0.000 description 1
• 125000001309 chloro group Chemical group Cl* 0.000 description 1
• 150000001924 cycloalkanes Chemical class 0.000 description 1
• 206010061428 decreased appetite Diseases 0.000 description 1
• 239000000543 intermediate Substances 0.000 description 1
• 239000007788 liquid Substances 0.000 description 1
• 239000000155 melt Substances 0.000 description 1
• 238000004904 shortening Methods 0.000 description 1
• 239000007787 solid Substances 0.000 description 1
• 238000003756 stirring Methods 0.000 description 1