Diisopropylethylamine → N-(6-Chloro-4-o-tolyl-pyridin-3-yl)-N-methyl-3,5-bis-trifluoromethyl-benzamide

HRID 877970Notes

Reaction equation

HRID 877970 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1)[C:6](Cl)=[O:7].[Cl:18][C:19]1[N:24]=[CH:23][C:22]([NH:25][CH3:26])=[C:21]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[CH3:33])[CH:20]=1.CCN(C(C)C)C(C)C>C1COCC1>[Cl:18][C:19]1[N:24]=[CH:23][C:22]([N:25]([CH3:26])[C:6](=[O:7])[C:5]2[CH:4]=[C:3]([C:2]([F:17])([F:16])[F:1])[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=2)=[C:21]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[CH3:33])[CH:20]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1018563,5-Bis(trifluoromethyl)benzoyl chlorideHCID 577104436-chloro-N-methyl-4-(2-methylphenyl)pyridin-3-amine

Product 1

HCID 60197100N-(6-Chloro-4-o-tolyl-pyridin-3-yl)-N-methyl-3,5-bis-trifluoromethyl-benzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3,5-Bis-trifluoromethylbenzoyl chloride (76 mg, 0.28 mmol, CAS RN 1271-19-8) was added to a solution of 6-chloro-N-methyl-4-o-tolylpyridin-3-amine (30 mg, 0.13 mmol, prepared as described in WO2005/002577) and DIPEA (50 μL, 0.29 mmol) in THF (1.5 mL). The reaction mixture was stirred overnight, filtered and all volatiles removed in vacuo. The desired product was isolated by flash chromatography on silica gel (25% EtOAc in n-hexane) as a waxy solid (48 mg, 79%). MS (ESI): m/z=472.9 [M+H]+.

Workup

  1. filtrationfiltered
  2. customall volatiles removed in vacuo

Sources & evidence

ORD record
ord-51379514f265442e837517e7b307a6c4
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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