Triethylamine → HCID 9916144, compound

HRID 2260514Notes

Reaction equation

[CH2:1]([O:8][CH2:9][CH2:10][NH:11][C@H:12]([CH3:29])[C@:13]([C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=1[F:28])([OH:20])[CH2:14][N:15]1[CH:19]=[N:18][CH:17]=[N:16]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[F:37][C:38]([F:49])([F:48])[C:39]1[CH:47]=[CH:46][C:42]([C:43](Cl)=[O:44])=[CH:41][CH:40]=1>C(Cl)Cl>[F:28][C:22]1[CH:23]=[C:24]([F:27])[CH:25]=[CH:26][C:21]=1[C@:13]([OH:20])([C@H:12]([N:11]([C:43](=[O:44])[C:42]1[CH:46]=[CH:47][C:39]([C:38]([F:37])([F:48])[F:49])=[CH:40][CH:41]=1)[CH2:10][CH2:9][O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH3:29])[CH2:14][N:15]1[CH:19]=[N:18][CH:17]=[N:16]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (2R*,3R*)-3-[(2-benzyloxyethyl)amino]-2-[2,4-difluorophenyl]-1-(1H-1,2,4-triazol-1-yl)-2-butanol (4.40 g, 11.4 mmol) (obtained as described in reference example 2) in CH2Cl2 (40 mL) was added triethylamine (1.74 mL, 12.5 mmol). The resulting mixture was cooled in an ice bath and a solution of 4-(trifluoromethyl)benzoyl chloride (2.61 g, 12.5 mmol) in CH2Cl2 (5 mL) was carefully added and the mixture was stirred for 1 h at 0° C. and then for 18 h at room temperature. The resulting solution was diluted with CH2Cl2 and washed with 5% aqueous NaHCO3 solution. The organic phase was separated, dried over Na2SO4 and the solvent was removed, to afford a thick oil (9.17 g) that was purified by chromatography on silica gel (EtOAc: hexane 1:1). The title compound of the example was obtained as a white foam.

Workup

temperatureThe resulting mixture was cooled in an ice bath
waitfor 18 h at room temperature
washwashed with 5% aqueous NaHCO3 solution
customThe organic phase was separated
dry with materialdried over Na2SO4
customthe solvent was removed

Sources & evidence

ORD record: ord-f5af74f0570d4b5ca547c6fa4592001d
Source dataset: uspto-grants-1995_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05478826

Reaction notes

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