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

HRID 1806517ノート

反応式

HRID 1806517 の反応式
[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]

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 679Dimethyl Sulfoxide溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-6f498d7b521c406a961dc2bd271791d6
出典データセット
uspto-grants-2013_01
特許番号
US08354406B2

反応ノート

読み込み中…