Cyclohexylamine → 2-methyl-1-[(S)-1-(tetrahydro-furan-2-yl)methyl]-5-(2-trifluoromethoxy-phenyl)-1H-pyrrole-3-carboxylic acid cyclohexylamide

HRID 229862

反応式

HRID 229862 の反応式
[CH3:1][C:2]1[N:3]([CH2:21][C@@H:22]2[CH2:26][CH2:25][CH2:24][O:23]2)[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][C:17]([F:20])([F:19])[F:18])=[CH:5][C:6]=1[C:7](O)=[O:8].CN(C(O[N:35]1N=N[C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][C:36]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)C(C)C)(C)C.C1(N)CCCCC1>CN(C)C=O>[CH:36]1([NH:35][C:7]([C:6]2[CH:5]=[C:4]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[O:16][C:17]([F:18])([F:19])[F:20])[N:3]([CH2:21][C@@H:22]3[CH2:26][CH2:25][CH2:24][O:23]3)[C:2]=2[CH3:1])=[O:8])[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1

参加物

6

反応物 4

HCID 7965CyclohexylamineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 690199812-methyl-1-[(S)-1-(tetrahydro-furan-2-yl)methyl]-5-(2-trifluoromethoxy-phenyl)-1H-pyrrole-3-carboxylic acid

生成物 1

HCID 116193132-methyl-1-[(S)-1-(tetrahydro-furan-2-yl)methyl]-5-(2-trifluoromethoxy-phenyl)-1H-pyrrole-3-carboxylic acid cyclohexylamide収率 74.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 77 mg of 2-methyl-1-[(S)-1-(tetrahydro-furan-2-yl)methyl]-5-(2-trifluoromethoxy-phenyl)-1H-pyrrole-3-carboxylic acid in 3 ml of dimethylformamide were added 74 mg of TBTU, 179 μl of N,N-diisopropylethylamine and 26 μl of cyclohexylamine and the reaction mixture was stirred at ambient temperature for 18 hours. After such time the reaction mixture was then concentrated in vacuo and purified by column chromatography (SiO2, heptane/ethyl acetate) to give 70 mg of the title compound as a colorless solid, MS (ISP) 451.5 (M+H)+.

後処理

  1. concentrationAfter such time the reaction mixture was then concentrated in vacuo
  2. custompurified by column chromatography (SiO2, heptane/ethyl acetate)

出典と根拠

ORDレコード
ord-98c6549fcfc146cfbf597b08fa7994f7
出典データセット
uspto-grants-2009_07
特許番号
US07563910B2

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