2-(3,5-Bis(trifluoromethyl)phenyl)-2-methylpropanoyl chloride → HCID 86584781, compound

HRID 1835320Notes

Reaction equation

HRID 1835320 reaction equation
[CH2:1]([O:8][C:9](=[O:33])[N:10]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:11]1[CH:16]=[C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH3:23])[C:14]([NH:24][CH3:25])=[CH:13][N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:34][C:35]([F:53])([F:52])[C:36]1[CH:37]=[C:38]([C:46]([CH3:51])([CH3:50])[C:47](Cl)=[O:48])[CH:39]=[C:40]([C:42]([F:45])([F:44])[F:43])[CH:41]=1>ClCCl.C(N(C(C)C)C(C)C)C>[CH2:1]([O:8][C:9](=[O:33])[N:10]([CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:11]1[CH:16]=[C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH3:23])[C:14]([N:24]([C:47](=[O:48])[C:46]([C:38]2[CH:37]=[C:36]([C:35]([F:34])([F:52])[F:53])[CH:41]=[C:40]([C:42]([F:43])([F:44])[F:45])[CH:39]=2)([CH3:51])[CH3:50])[CH3:25])=[CH:13][N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 112671412-(3,5-Bis(trifluoromethyl)phenyl)-2-methylpropanoyl chlorideHCID 53824026HCID 53824026, compound

Product 1

HCID 86584781HCID 86584781, compoundYield 63.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 81531DiisopropylethylamineSolvent

Procedure

To a solution of 1.075 g (2.5 mmol) benzyl-(5-methylamino-4-o-tolyl-pyridin-2-yl)-carbamic acid benzyl ester in 10 ml dichloromethane and 1 ml N-ethyldiisopropylamine was added dropwise at 0° C. a solution of 1.15 g (3.5 mmol) 2-(3,5-bis-trifluoromethyl-phenyl)-2-methyl-propionic acid chloride in 2 ml dichloromethane and the mixture was stirred for 3 h at room temperature. The solution was washed with water (20 ml), saturated aqueous sodium hydrogencarbonate solution (20 ml) and brine (20 ml), dried (magnesium sulfate) and evaporated. Chromatography of the residue afforded 1.15 g (62%) of the title compound as a yellow oil.

Workup

  1. washThe solution was washed with water (20 ml), saturated aqueous sodium hydrogencarbonate solution (20 ml) and brine (20 ml)
  2. dry with materialdried (magnesium sulfate)
  3. customevaporated

Sources & evidence

ORD record
ord-5d36386774664019bafa5036db3e9f41
Source dataset
uspto-grants-2004_08
Patent number
US06770637B2

Reaction notes

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