Benzoyl chloride → N-{3-Chloro-4-[2-(2-chloro-pyridin-4-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-phenyl}-benzamide

HRID 333835Notes

Reaction equation

HRID 333835 reaction equation
C(N(CC)C(C)C)(C)C.[C:10](Cl)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[NH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH:26]([CH3:40])[C:27]([C:33]2[CH:38]=[CH:37][N:36]=[C:35]([Cl:39])[CH:34]=2)([OH:32])[C:28]([F:31])([F:30])[F:29])=[C:22]([Cl:41])[CH:21]=1>C(Cl)Cl>[Cl:41][C:22]1[CH:21]=[C:20]([NH:19][C:10](=[O:17])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:25]=[CH:24][C:23]=1[CH:26]([CH3:40])[C:27]([C:33]1[CH:38]=[CH:37][N:36]=[C:35]([Cl:39])[CH:34]=1)([OH:32])[C:28]([F:31])([F:30])[F:29]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 81531DiisopropylethylamineHCID 866291093-(4-Amino-2-chloro-phenyl)-2-(2-chloro-pyridin-4-yl)-1,1,1-trifluoro-butan-2-ol

Product 1

HCID 25254771N-{3-Chloro-4-[2-(2-chloro-pyridin-4-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-phenyl}-benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N,N-diisopropylethylamine (0.117 ml) and benzoyl chloride (0.024 ml) were added to a solution of 3-(4-amino-2-chloro-phenyl)-2-(2-chloro-pyridin-4-yl)-1,1,1-trifluoro-butan-2-ol (25 mg) in DCM (3 ml). The mixture was stirred at room temperature for 2 h and then concentrated in vacuo. Purification by preparative HPLC (Phenomenex Gemini Axia-C18 column, solvent gradient 30-95% CH3CN in 0.1% HCOOH[aq]) gave the title compound (35 mg) as a white foam. MS (m/e)=469.2 [M+H+].

Workup

  1. concentrationconcentrated in vacuo
  2. customPurification by preparative HPLC (Phenomenex Gemini Axia-C18 column, solvent gradient 30-95% CH3CN in 0.1% HCOOH[aq])

Sources & evidence

ORD record
ord-469a18d9233240c582b5203cba474a49
Source dataset
uspto-grants-2014_11
Patent number
US08883786B2

Reaction notes

Loading…