Diisopropylethylamine → HCID 86670686, compound

HRID 877975Notes

Reaction equation

HRID 877975 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]([N:5]([CH3:21])[C:6]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])[C:9]([NH:19][CH3:20])=[CH:8][N:7]=1)=[O:4].CCN(C(C)C)C(C)C.[F:33][C:34]([F:49])([F:48])[C:35]1[CH:36]=[C:37]([CH:41]=[C:42]([C:44]([F:47])([F:46])[F:45])[CH:43]=1)[C:38](Cl)=[O:39]>C1COCC1>[CH3:20][N:19]([C:9]1[CH:8]=[N:7][C:6]([N:5]([CH3:21])[C:3](=[O:4])[C:2]([F:1])([F:22])[F:23])=[CH:11][C:10]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:18])[C:38](=[O:39])[C:37]1[CH:41]=[C:42]([C:44]([F:45])([F:46])[F:47])[CH:43]=[C:35]([C:34]([F:33])([F:48])[F:49])[CH:36]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1018563,5-Bis(trifluoromethyl)benzoyl chlorideHCID 86670687HCID 86670687, compound

Product 1

HCID 86670686HCID 86670686, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2,2,2-Trifluoro-N-methyl-N-(5-(methylamino)-4-o-tolylpyridin-2-yl)acetamide (46 mg, 0.14 mmol) and DIPEA (61 μL, 0.35 mmol) in THF (1.5 mL) were treated with 3,5-bis-trifluoromethylbenzoyl chloride (51 μL, 0.28 mmol, CAS RN 1271-19-8). 3,5-Bis-trifluorobenzoyl chloride (25 μL, 0.14 mmol, CAS RN 1271-19-8) was added again at 90 min. and 4 hours. The reaction mixture was stirred for 60 hours and then evaporated to dryness. From the resulting residue, the product N-methyl-N-(4-o-tolyl-6-(2,2,2-trifluoro-N-methylacetamido)pyridin-3-yl)-3,5-bis(trifluoromethyl)benzamide was isolated by flash chromatography on silica gel (33-50% EtOAc in n-hexane) as a foam (70 mg, 87% over two steps). The compound was used in the next step without further purification.

Workup

  1. customevaporated to dryness

Sources & evidence

ORD record
ord-b0035478f2ea4973a429ebc789262a62
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

Loading…