Water → HCID 67484516, compound

HRID 1633959Notes

Reaction equation

Cl.[CH3:2][O:3][C:4](=[O:38])[CH2:5][CH2:6][NH:7][C:8](=[O:37])[C:9]1[CH:14]=[CH:13][C:12]([CH:15]([NH:22][C:23]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][C:33]([F:36])([F:35])[F:34])=[CH:28][CH:27]=2)=[O:24])[CH:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)=[CH:11][CH:10]=1.C(N(C(C)C)CC)(C)C.[CH:48]1([C:51](Cl)=[O:52])[CH2:50][CH2:49]1.O>CN(C=O)C.C(OCC)(=O)C>[CH3:2][O:3][C:4](=[O:38])[CH2:5][CH2:6][NH:7][C:8](=[O:37])[C:9]1[CH:14]=[CH:13][C:12]([CH:15]([NH:22][C:23]([NH:25][C:26]2[CH:27]=[CH:28][C:29]([O:32][C:33]([F:34])([F:35])[F:36])=[CH:30][CH:31]=2)=[O:24])[CH:16]2[CH2:17][CH2:18][N:19]([C:51]([CH:48]3[CH2:50][CH2:49]3)=[O:52])[CH2:20][CH2:21]2)=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 3-{4-[1-piperidin-4-yl-3-(4-trifluoromethoxyphenyl)ureidomethyl]benzoyl-amino}propionic acid methyl ester hydrochloride (0.20 g) in DMF (5 mL) was added diisopropylethylamine (0.30 mL) and cyclopropylcarboxylic acid chloride (0.16 mL). The mixture was stirred at 25° C. overnight. Water (100 mL) and ethyl acetate (100 mL) were added, the phases separated and the organic phase was washed with a solution of NH4Cl (sat., 2×50 mL) and water (50 mL). Upon drying with MgSO4 the solvent was evaporated and the residue purified by column chromatography.

Workup

customthe phases separated
washthe organic phase was washed with a solution of NH4Cl (sat., 2×50 mL) and water (50 mL)
dry with materialUpon drying with MgSO4 the solvent
customwas evaporated
customthe residue purified by column chromatography

Sources & evidence

ORD record: ord-60b56890aba34c08a190c73433110237
Source dataset: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06503949B1

Reaction notes

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