Diisopropylethylamine → N-[6-(4-Methanesulfonyl-piperazin-1-yl)-4-o-tolyl-pyridin-3-yl]-N-methyl-3,5-bis-trifluoromethyl-benzamide

HRID 877979Notes

Reaction equation

HRID 877979 reaction equation
[CH3:1][NH:2][C:3]1[CH:4]=[N:5][C:6]([N:16]2[CH2:21][CH2:20][N:19]([S:22]([CH3:25])(=[O:24])=[O:23])[CH2:18][CH2:17]2)=[CH:7][C:8]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH3:15].CCN(C(C)C)C(C)C.[F:35][C:36]([F:51])([F:50])[C:37]1[CH:38]=[C:39]([CH:43]=[C:44]([C:46]([F:49])([F:48])[F:47])[CH:45]=1)[C:40](Cl)=[O:41]>C(Cl)Cl>[CH3:25][S:22]([N:19]1[CH2:18][CH2:17][N:16]([C:6]2[N:5]=[CH:4][C:3]([N:2]([CH3:1])[C:40](=[O:41])[C:39]3[CH:38]=[C:37]([C:36]([F:51])([F:50])[F:35])[CH:45]=[C:44]([C:46]([F:49])([F:48])[F:47])[CH:43]=3)=[C:8]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[CH3:15])[CH:7]=2)[CH2:21][CH2:20]1)(=[O:24])=[O:23]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1018563,5-Bis(trifluoromethyl)benzoyl chlorideHCID 70663108N-methyl-6-(4-(methylsulfonyl)piperazin-1-yl)-4-o-tolylpyridin-3-amine

Product 1

HCID 60196995N-[6-(4-Methanesulfonyl-piperazin-1-yl)-4-o-tolyl-pyridin-3-yl]-N-methyl-3,5-bis-trifluoromethyl-benzamideYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-methyl-6-(4-(methylsulfonyl)piperazin-1-yl)-4-o-tolylpyridin-3-amine (37 mg, 0.10 mmol) and DIPEA (50 μL, 0.29 mmol) in CH2Cl2 was treated with 3,5-bis-trifluoromethylbenzoyl chloride (43 mg, 0.15 mmol, CAS RN 1271-19-8). After stirring for 1 h, the reaction mixture was loaded directly onto a silica gel column. Elution with 50% EtOAc in n-hexane afforded the title compound as a yellow solid (48 mg, 80%). MS (ESI): m/z=601.0 [M+H]+.

Workup

  1. washElution with 50% EtOAc in n-hexane

Sources & evidence

ORD record
ord-fe6b202d259545ca9a85cc0bae27337b
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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