Potassium Carbonate → HCID 68805089, compound

HRID 887900Notes

Reaction equation

HRID 887900 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]([O:12][CH3:13])=[O:11])=[C:4]([NH:14][C:15]([NH:17][C:18](=[O:28])[C:19]2[CH:24]=[C:23]([F:25])[C:22]([F:26])=[CH:21][C:20]=2[Cl:27])=[O:16])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:36]([O:38][C:39]1[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][CH:40]=1)=[O:37]>CN(C)C=O>[Cl:27][C:20]1[CH:21]=[C:22]([F:26])[C:23]([F:25])=[CH:24][C:19]=1[C:18]([NH:17][C:15](=[O:16])[NH:14][C:4]1[CH:3]=[C:2]([NH:1][C:36]([O:38][C:39]2[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][CH:40]=2)=[O:37])[CH:7]=[CH:6][C:5]=1/[CH:8]=[CH:9]/[C:10]([O:12][CH3:13])=[O:11])=[O:28]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1390594-Chlorophenyl chloroformateHCID 68806941HCID 68806941, compound

Product 1

HCID 68805089HCID 68805089, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

100 mg (0.24 mmol) of methyl 3-{4-amino-2-[3-(2-chloro-4,5-difluorobenzoyl)-ureido]phenyl}acrylate (example 54b) were reacted in 2 ml of dimethylformamide with potassium carbonate and 4-chlorophenyl chloroformate. The precipitate resulting after 4 hours was filtered off with suction. Preparative HPLC (column: Waters Xterra™MS C18, 5 μm, 30×100 mm, mobile phases: A: H2O+0.2% trifluoroacetic acid, B: acetonitrile, gradient: 2.5 minutes 90% A/10% B to 17.5 minutes 10% A/90% B) resulted in 12 mg (9%) of the desired product.

Workup

  1. customThe precipitate resulting after 4 hours
  2. filtrationwas filtered off with suction

Sources & evidence

ORD record
ord-8b9c3e2566d644579f97887c8245807e
Source dataset
uspto-grants-2012_08
Patent number
US08247452B2

Reaction notes

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