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

HRID 2239008노트

반응식

HRID 2239008 반응식
[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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-87e9d3298bc64dc3964fcd063a202b4b
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07718798B2

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