Formaldehyde → 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-(5-{[[2-(ethylthio)ethyl](methyl)amino]methyl}-3-thienyl)-1H-indole-7-carboxamide

HRID 1806517노트

반응식

HRID 1806517 반응식
[CH:1]([C:3]1[S:7][CH:6]=[C:5]([C:8]2[CH:9]=[C:10]3[C:14](=[C:15]([C:17]([NH2:19])=[O:18])[CH:16]=2)[NH:13][CH:12]=[C:11]3[CH:20]2[CH2:25][CH2:24][N:23]([S:26]([CH:29](C)[CH3:30])(=[O:28])=[O:27])[CH2:22][CH2:21]2)[CH:4]=1)=O.[CH2:32]([S:34][CH2:35][CH2:36][NH2:37])[CH3:33].[C:38](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([BH3-])#N.[Na+].C=O>CS(C)=O.C(O)(=O)C>[CH2:29]([S:26]([N:23]1[CH2:22][CH2:21][CH:20]([C:11]2[C:10]3[C:14](=[C:15]([C:17]([NH2:19])=[O:18])[CH:16]=[C:8]([C:5]4[CH:4]=[C:3]([CH2:1][N:37]([CH2:36][CH2:35][S:34][CH2:32][CH3:33])[CH3:38])[S:7][CH:6]=4)[CH:9]=3)[NH:13][CH:12]=2)[CH2:25][CH2:24]1)(=[O:27])=[O:28])[CH3:30]

참가 물질

8

반응물 5

HCID 712FormaldehydeHCID 148011Ethanamine, 2-(ethylthio)-HCID 5003444Sodium cyanoborohydrideHCID 5049666Sodium triacetoxyborohydrideHCID 577327835-(5-formyl-3-thienyl)-3-{1-[(1-methylethyl)sulfonyl]-4-piperidinyl}-1H-indole-7-carboxamide

생성물 1

HCID 577328503-[1-(ethylsulfonyl)-4-piperidinyl]-5-(5-{[[2-(ethylthio)ethyl](methyl)amino]methyl}-3-thienyl)-1H-indole-7-carboxamide수율 14.2%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 679Dimethyl Sulfoxide용매

실험 절차

To a solution of 5-(5-formyl-3-thienyl)-3-{1-[(1-methylethyl)sulfonyl]-4-piperidinyl}-1H-indole-7-carboxamide (40 mg, 0.09 mmol) in DMSO (2 mL) was added [2-(ethylthio)ethyl]amine (105 mg, 1 mmol), acetic acid (50 μL), and sodium triacetoxyborohydride (212 mg, 1.0 mmol). The resulting mixture was stirred overnight. To the mixture was added sodium cyanoborohydride (80 mg, 1.2 mmol) and stirred overnight followed by addition of formaldehyde (100 μL, 1.2 mmol). The mixture was then stirred for an additional 3 h. It was then purified by Gilson Preparatory HPLC to give 7.0 mg of the title compound.

후처리

  1. stirringstirred overnight
  2. stirringThe mixture was then stirred for an additional 3 h
  3. customIt was then purified by Gilson Preparatory HPLC

출처 및 근거

ORD 기록
ord-6f498d7b521c406a961dc2bd271791d6
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08354406B2

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