Water → HCID 10319353, compound

HRID 887897Notes

Reaction equation

HRID 887897 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[NH:11][C:12]([NH:14][C:15](=[O:24])[C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=1[Cl:23])=[O:13].N1C=CC=CC=1.Cl[C:32]([O:34][CH3:35])=[O:33].O>CN1CCCC1=O.C(O)(=O)C>[Cl:23][C:17]1[CH:18]=[C:19]([F:22])[CH:20]=[CH:21][C:16]=1[C:15]([NH:14][C:12](=[O:13])[NH:11][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:2]=1[NH:1][C:32]([O:34][CH3:35])=[O:33])[C:6]([OH:8])=[O:7])=[O:24]

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 6586Methyl chloroformateHCID 68805970HCID 68805970, compound

Product 1

HCID 10319353HCID 10319353, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

28 mg (0.08 mmol) of 4-amino-3-[3-(2-chloro-4-fluorobenzoyl)ureido]benzoic acid were dissolved in 0.5 ml of N-methyl-2-pyrrolidinone and stirred with 0.02 ml (0.24 mmol) of pyridine and 0.007 ml of methyl chloroformate at room temperature for 4 hours. Water and acetic acid were added, and the resulting precipitate was filtered off with suction. 18 mg (55%) of the desired product were obtained.

Workup

  1. filtrationthe resulting precipitate was filtered off with suction

Sources & evidence

ORD record
ord-c7090f6a1d03490c9a9a95849a726c50
Source dataset
uspto-grants-2012_08
Patent number
US08247452B2

Reaction notes

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