Benzylamine → HCID 86651104, compound

HRID 1810287Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:39])[CH2:5][C:6]1[CH:7]=[C:8]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][C:15]=2[CH2:24][N:25]([CH2:37][CH3:38])[C:26](=[N:34][C:35]#[N:36])OC2C=CC=CC=2)[C:9]([O:12][CH3:13])=[CH:10][CH:11]=1)[CH3:2].[CH2:40]([NH2:47])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>CCO>[CH2:1]([O:3][C:4](=[O:39])[CH2:5][C:6]1[CH:7]=[C:8]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][C:15]=2[CH2:24][N:25]([CH2:37][CH3:38])[C:26]([NH:34][C:35]#[N:36])=[N:47][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:9]([O:12][CH3:13])=[CH:10][CH:11]=1)[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

[2′-(3-Cyano-1-ethyl-2-phenyl-isoureidomethyl)-6-methoxy-4′-trifluoromethyl-biphenyl-3-yl]-acetic acid ethyl ester (0.10 g, 0.17 mmol) and benzylamine (0.04 mL, 0.34 mmol) were combined in EtOH (1 mL) and heated to 60° C. The reaction was monitored by analytical LCMS, and additional benzylamine (0.04 mL, 0.34 mmol) was added to push the reaction to completion. Further benzylamine (0.10 mL, 0.92 mmol) was added, and the reaction was heated for a total of 48 hours. The mixture was partitioned between EtOAc and H2O, and the aqueous layer was extracted with EtOAc. The combined organic layers were concentrated and purified by silica gel chromatography (0-50% EtOAc in hexanes) to give the title compound.

Workup

additionwas added
customthe reaction to completion
temperaturethe reaction was heated for a total of 48 hours
customThe mixture was partitioned between EtOAc and H2O
extractionthe aqueous layer was extracted with EtOAc
concentrationThe combined organic layers were concentrated
custompurified by silica gel chromatography (0-50% EtOAc in hexanes)

Sources & evidence

ORD record: ord-0fe2ebbaf8884c22a7adc9e3136234f2
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362044B2

Reaction notes

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