4-Methylmorpholine → 6-chloro-N5-cyclopropyl-N2-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-1H-benzimidazole-2,5-dicarboxamide

HRID 514260

반응식

HRID 514260 반응식
[F:1][C:2]([F:16])([F:15])[CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:14])([F:13])[F:12])[CH:6]=1)[NH2:4].[Cl:17][C:18]1[C:19]([C:30](=[O:35])[NH:31][CH:32]2[CH2:34][CH2:33]2)=[CH:20][C:21]2[N:25]=[C:24]([C:26](O)=[O:27])[NH:23][C:22]=2[CH:29]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.CN1CCOCC1>CN(C)C=O.C(OCC)(=O)C>[Cl:17][C:18]1[C:19]([C:30]([NH:31][CH:32]2[CH2:34][CH2:33]2)=[O:35])=[CH:20][C:21]2[N:25]=[C:24]([C:26]([NH:4][CH:3]([C:5]3[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:12])([F:13])[F:14])[CH:6]=3)[C:2]([F:15])([F:16])[F:1])=[O:27])[NH:23][C:22]=2[CH:29]=1

참가 물질

7

반응물 4

HCID 79724-MethylmorpholineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 438251722,2,2-Trifluoro-1-(3-(trifluoromethyl)phenyl)ethanamineHCID 682930886-chloro-5-(cyclopropylcarbamoyl)-1H-benzimidazole-2-carboxylic acid

생성물 1

HCID 867139816-chloro-N5-cyclopropyl-N2-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-1H-benzimidazole-2,5-dicarboxamide수율 58%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

2,2,2-Trifluoro-1-[3-(trifluoromethyl)phenyl]ethanamine (0.23 g, 0.82 mmol) was dissolved in N,N-dimethylformamide (4 ml), and 6-chloro-5-(cyclopropylcarbamoyl)-1H-benzimidazole-2-carboxylic acid (0.23 g, 0.82 mmol), N-[(1H-benzotriazol-1-yloxy)(dimethylamino)methylene]-N-methylmethanaminium hexafluorophosphate (0.31 g, 0.82 mmol) and 4-methylmorpholine (0.25 g, 2.47 mmol) were added. The reaction mixture was stirred at room temperature for 16 h and then ethyl acetate was added. The organic phase was washed with saturated sodium hydrogencarbonate solution and saturated sodium chloride solution and dried over sodium sulphate, and the solvent was removed under reduced pressure. The residue was chromatographed with cyclohexane/ethyl acetate (1/1) and gave 0.24 g (57% of theory) of 6-chloro-N5-cyclopropyl-N2-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-1H-benzimidazole-2,5-dicarboxamide.

후처리

  1. washThe organic phase was washed with saturated sodium hydrogencarbonate solution and saturated sodium chloride solution
  2. dry with materialdried over sodium sulphate
  3. customthe solvent was removed under reduced pressure
  4. customThe residue was chromatographed with cyclohexane/ethyl acetate (1/1)

출처 및 근거

ORD 기록
ord-fa81a40ed8874750b358d164afa61467
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09107411B2

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