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

HRID 1189655
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HRID 1189655 반응식
[Cl:1][C:2]1[C:7]([CH2:8][NH:9][C:10](=[O:15])[C:11]([CH3:14])([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]([OH:30])=O)=[CH:27][C:20]=2[N:19]=1.ClC(N(C)C)=C(C)C.[Cl:49][C:50]1[CH:51]=[C:52]([CH:54]=[CH:55][C:56]=1[F:57])[NH2:53].CCN(C(C)C)C(C)C>CC#N>[Cl:49][C:50]1[CH:51]=[C:52]([NH:53][C:28]([C:26]2[C:25]([N:31]3[CH2:32][CH2:33][CH:34]([C:37]([F:39])([F:38])[F:40])[CH2:35][CH2:36]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]([CH3:14])([CH3:13])[CH3:12])[C:2]=4[Cl:1])=[N:19][C:20]=3[CH:27]=2)=[O:30])[CH:54]=[CH:55][C:56]=1[F:57]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 97083-Chloro-4-fluoroanilineHCID 81531DiisopropylethylamineHCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 679575572-{2,6-Dichloro-3-[(2,2-dimethyl-propionylamino)-methyl]-phenylamino}-6-[4-trifluoromethyl-piperidinyl]-1-methyl-1H-benzimidazole-5-carboxylic acid

생성물 1

HCID 86666467
N-(3-Chloro-4-fluoro-phenyl)-2-{2,6-dichloro-3-[(2,2-dimethyl-propionylamino)-methyl]-phenylamino}-6-[4-trifluoromethyl-piperidinyl]-1-methyl-1H-benzimidazole-5-carboxylic acid amide

시약·촉매·용매 1

HCID 6342Acetonitrile용매2회

실험 절차

A mixture of 2-{2,6-dichloro-3-[(2,2-dimethyl-propionylamino)-methyl]-phenylamino}-6-[4-trifluoromethyl-piperidinyl]-1-methyl-1H-benzimidazole-5-carboxylic acid (72 mg, 0.120 mmol), (1-chloro-2-methyl-propenyl)-dimethylamine (33 mg, 0.25 mmol) and MeCN (2 mL) is stirred for 20 min. This mixture is added to 3-chloro-4-fluoro-aniline (36 mg, 0.25 mmol) and DIPEA (129 μL, 0.75 mmol) in MeCN (3 mL) and it is stirred overnight. The mixture is concentrated and the residue is taken up in DMF (2 mL) and purified by reverse phase HPLC.

후처리

  1. stirringis stirred overnight
  2. concentrationThe mixture is concentrated
  3. custompurified by reverse phase HPLC

출처 및 근거

ORD 기록
ord-d40c6c15138c436ebfaf7299b851fa04
출처 데이터셋
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08674113B2

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