Pyridine → HCID 86653072, compound

HRID 339108Notes

Reaction equation

[NH2:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:11]([NH:13][CH:14]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=3)[C:15]([F:18])([F:17])[F:16])=[O:12])=[CH:8][C:7]=2[CH:29]=1.N1C=CC=CC=1.[C:36](Cl)(=[O:38])[CH3:37]>ClCCl.C(OCC)(=O)C>[C:36]([NH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:11]([NH:13][CH:14]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:26])[F:27])[CH:20]=3)[C:15]([F:16])([F:17])[F:18])=[O:12])=[CH:8][C:7]=2[CH:29]=1)(=[O:38])[CH3:37]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 5-(aminomethyl)-N-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-1-benzofuran-2-carboxamide (50 mg, 0.12 mmol) in dichloromethane (1 ml) was admixed with pyridine (0.01 ml) and cooled to 0° C. Then acetyl chloride (9 μl, 0.12 mmol) was added dropwise and the mixture was warmed up to room temperature overnight. The mixture was diluted with ethyl acetate and washed with hydrochloric acid (1 M). The organic phase was dried over sodium sulphate, filtered and concentrated under reduced pressure. The residue was chromatographed on a preparative HPLC with water/acetonitrile as the eluent (gradient=43 min from 10% acetonitrile in water to 100% acetonitrile).

Workup

temperaturethe mixture was warmed up to room temperature overnight
washwashed with hydrochloric acid (1 M)
dry with materialThe organic phase was dried over sodium sulphate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was chromatographed on a preparative HPLC with water/acetonitrile as the eluent (gradient=43 min from 10% acetonitrile in water to 100% acetonitrile)

Sources & evidence

ORD record: ord-8db08294f0d5479b87a199476d5a4e9f
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889878B2

Reaction notes

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