Diisopropylethylamine → 1,1-Dimethylethyl 4-(5-trifluoromethyl-6-chloro-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-1-piperidinecarboxylate

HRID 2064167Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[C:5]([Cl:12])=[CH:4][C:3]=1[NH:13][CH:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1.Cl[C:28](Cl)([O:30]C(=O)OC(Cl)(Cl)Cl)Cl.C(N(C(C)C)CC)(C)C>ClCCl>[F:10][C:8]([F:11])([F:9])[C:6]1[C:5]([Cl:12])=[CH:4][C:3]2[N:13]([CH:14]3[CH2:15][CH2:16][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:18][CH2:19]3)[C:28](=[O:30])[NH:1][C:2]=2[CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

1,1-Dimethylethyl 4-[(2-amino-5-chloro-4-trifluoromethylphenyl)amino]-1-piperidinecarboxylate (D62, 2.2 g) was dissolved in 25 ml of dichloromethane at 0° C. and triphosgene (0.6 g) and diisopropylethylamine (1.0 ml) were added and the mixture was stirred at 0° C. for 1 h, then washed with aqueous citric acid, dried over MgSO4, filtered and evaporated The product was chromatographed on silica gel eluting with methanol-dichloromethane mixtures, then crystallised from diethyl ether to yield the subtitle compound, 1.0 g.

Workup

washwashed with aqueous citric acid
dry with materialdried over MgSO4
filtrationfiltered
customevaporated The product
customwas chromatographed on silica gel eluting with methanol-dichloromethane mixtures
customcrystallised from diethyl ether

Sources & evidence

ORD record: ord-c918bcbcc1ee4d6588d5201ee91035c6
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288412B2

Reaction notes

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