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

HRID 1168335Notes

Reaction equation

HRID 1168335 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. MS m/e (%): 720 (M+H+, 100).

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-de5c4abf0309465b9b91bbb4896ec1ee
Source dataset
uspto-grants-2003_09
Patent number
US06624176B2

Reaction notes

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