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

HRID 514260

反応式

HRID 514260 の反応式
[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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-fa81a40ed8874750b358d164afa61467
出典データセット
uspto-grants-2015_08
特許番号
US09107411B2

関連ノート

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