3-Chloro-4-fluoroaniline → N-(3-Chloro-4-fluoro-phenyl)-2-{2,6-dichloro-3-[(2-fluoro-2-methyl-propionylamino)-methyl]-phenylamino}-6-[4-trifluoromethyl-piperidinyl]-1-methyl-1H-benzimidazole-5-carboxylic acid amide

HRID 1189707Notes

Reaction equation

HRID 1189707 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][NH:9][C:10](=[O:15])[C:11]([F:14])([CH3:13])[CH3:12])=[CH:6][CH:5]=[C:4]([Cl:16])[C:3]=1[NH:17][C:18]1[N:22]([CH3:23])[C:21]2[CH:24]=[C:25]([N:31]3[CH2:36][CH2:35][CH:34]([C:37]([F:40])([F:39])[F:38])[CH2:33][CH2:32]3)[C:26]([C:28](O)=[O:29])=[CH:27][C:20]=2[N:19]=1.ClC(N(C)C)=C(C)C.CCN(C(C)C)C(C)C.[Cl:58][C:59]1[CH:60]=[C:61]([CH:63]=[CH:64][C:65]=1[F:66])[NH2:62]>CC#N>[Cl:58][C:59]1[CH:60]=[C:61]([NH:62][C:28]([C:26]2[C:25]([N:31]3[CH2:36][CH2:35][CH:34]([C:37]([F:40])([F:38])[F:39])[CH2:33][CH2:32]3)=[CH:24][C:21]3[N:22]([CH3:23])[C:18]([NH:17][C:3]4[C:4]([Cl:16])=[CH:5][CH:6]=[C:7]([CH2:8][NH:9][C:10](=[O:15])[C:11]([F:14])([CH3:13])[CH3:12])[C:2]=4[Cl:1])=[N:19][C:20]=3[CH:27]=2)=[O:29])[CH:63]=[CH:64][C:65]=1[F:66]

Participants

6

Reactant 4

HCID 97083-Chloro-4-fluoroanilineHCID 81531DiisopropylethylamineHCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 866664932-{2,6-Dichloro-3-[(2-fluoro-2-methyl-propionylamino)-methyl]-phenylamino}-6-[4-trifluoromethyl-piperidinyl]-1-methyl-1H-benzimidazole-5-carboxylic acid

Product 1

HCID 86666494N-(3-Chloro-4-fluoro-phenyl)-2-{2,6-dichloro-3-[(2-fluoro-2-methyl-propionylamino)-methyl]-phenylamino}-6-[4-trifluoromethyl-piperidinyl]-1-methyl-1H-benzimidazole-5-carboxylic acid amide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-{2,6-dichloro-3-[(2-fluoro-2-methyl-propionylamino)-methyl]-phenylamino}-6-[4-trifluoromethyl-piperidinyl]-1-methyl-1H-benzimidazole-5-carboxylic acid (60 mg, 0.100 mmol), (1-chloro-2-methyl-propenyl)-dimethylamine (33 mg, 0.25 mmol), DIPEA (86 μL, 0.50 mmol) and MeCN (2 mL) is stirred for 20 min. This mixture is added to 3-chloro-4-fluoro-aniline (0.200 mmol) and it is stirred overnight at rt. The mixture is directly purified via reverse phase HPLC. Yield: 39 mg. HPLC Rt=0.607 min (method F). MS m/z: 731 [M+H]+.

Workup

  1. stirringis stirred overnight at rt
  2. customThe mixture is directly purified via reverse phase HPLC

Sources & evidence

ORD record
ord-fd1542d2245e48d994902b5584bcfcf0
Source dataset
uspto-grants-2014_03
Patent number
US08674113B2

Reaction notes

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