Dichloromethane → 2-(2-(3-(chloromethyl)benzamido)-5-(piperidin-1-yl)phenyl)-N-(3-(trifluoromethyl)benzyl)-isonicotinamide

HRID 625267Notes

Reaction equation

[Cl:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](Cl)=[O:7].[F:12][C:13]([F:44])([F:43])[C:14]1[CH:15]=[C:16]([CH:40]=[CH:41][CH:42]=1)[CH2:17][NH:18][C:19](=[O:39])[C:20]1[CH:25]=[CH:24][N:23]=[C:22]([C:26]2[CH:31]=[C:30]([N:32]3[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]3)[CH:29]=[CH:28][C:27]=2[NH2:38])[CH:21]=1.C(N(C(C)C)CC)(C)C.ClCCl>C1COCC1>[Cl:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([NH:38][C:27]1[CH:28]=[CH:29][C:30]([N:32]2[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]2)=[CH:31][C:26]=1[C:22]1[CH:21]=[C:20]([CH:25]=[CH:24][N:23]=1)[C:19]([NH:18][CH2:17][C:16]1[CH:40]=[CH:41][CH:42]=[C:14]([C:13]([F:44])([F:12])[F:43])[CH:15]=1)=[O:39])=[O:7]

Participants

Conditions

Temperature: 25 °C

Procedure

3-(Chloromethyl)benzoyl chloride was added dropwise to a 0° C. solution of 900 mg of N-(3-(trifluoromethyl)benzyl)-2-(2-amino-5-(piperidin-1-yl)phenyl)isonicotinamide 4.1c 1.02 g of diisopropylethylamine in 10 mL of a 1:1 mixture of dichloromethane and THF. The mixture was warmed to 25° C. and stirred for 1 h, after which it was washed five times with aqueous hydrochloric acid, once with a saturated aqueous solution of sodium bicarbonate, and once with water. The solution was dried and the solvent was evaporated to give 1.24 g of product as a yellow solid.

Workup

washafter which it was washed five times with aqueous hydrochloric acid
customThe solution was dried
customthe solvent was evaporated

Sources & evidence

ORD record: ord-760d19221f64444691a299d9ad381748
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09301951B2

Reaction notes

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