1-Hydroxybenzotriazole → N-[2-(benzylthio)-3-thiomorpholinopropyl]-5-(3-methoxypropoxy)-7-[methyl(pyridin-2-ylsulfonyl)amino]-1H-indole-2-carboxamide

HRID 2239008ノート

反応式

HRID 2239008 の反応式
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]2[C:13](=[C:14]([N:16]([CH3:26])[S:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=3)(=[O:19])=[O:18])[CH:15]=1)[NH:12][C:11]([C:27]([OH:29])=O)=[CH:10]2.[CH2:30]([S:37][CH:38]([CH2:41][N:42]1[CH2:47][CH2:46][S:45][CH2:44][CH2:43]1)[CH2:39][NH2:40])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.N1(O)C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>O.CN(C)C=O>[CH2:30]([S:37][CH:38]([CH2:41][N:42]1[CH2:43][CH2:44][S:45][CH2:46][CH2:47]1)[CH2:39][NH:40][C:27]([C:11]1[NH:12][C:13]2[C:9]([CH:10]=1)=[CH:8][C:7]([O:6][CH2:5][CH2:4][CH2:3][O:2][CH3:1])=[CH:15][C:14]=2[N:16]([CH3:26])[S:17]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=1)(=[O:18])=[O:19])=[O:29])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

参加物

7

反応物 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 574762135-(3-methoxypropoxy)-7-[methyl(pyridin-2-ylsulfonyl)amino]-1H-indole-2-carboxylic acidHCID 574762142-(Benzylthio)-3-thiomorpholinopropan-1-amine

生成物 1

HCID 59303522N-[2-(benzylthio)-3-thiomorpholinopropyl]-5-(3-methoxypropoxy)-7-[methyl(pyridin-2-ylsulfonyl)amino]-1H-indole-2-carboxamide収率 78.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 5-(3-methoxypropoxy)-7-[methyl(pyridin-2-ylsulfonyl)amino]-1H-indole-2-carboxylic acid (330 mg), 2-(benzylthio)-3-thiomorpholinopropan-1-amine (200 mg), 1H-1,2,3-benzotriazol-1-ol (120 mg), N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (180 mg) and N,N-dimethylformamide (5 mL) was stirred at room temperature for 3 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed successively with saturated aqueous sodium hydrogencarbonate and saturated brine, dried (MgSO4), and concentrated. The obtained residue was subjected to silica gel column chromatography, and eluted with hexane-ethyl acetate (1:1-1:2, volume ratio) to give the title compound (380 mg, yield 78%) as a pale-yellow amorphous solid.

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed successively with saturated aqueous sodium hydrogencarbonate and saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. washeluted with hexane-ethyl acetate (1:1-1:2, volume ratio)

出典と根拠

ORDレコード
ord-87e9d3298bc64dc3964fcd063a202b4b
出典データセット
uspto-grants-2010_05
特許番号
US07718798B2

反応ノート

読み込み中…