Potassium Carbonate → 4'-{[5-(3-Cyano-benzyloxy)-4-hydroxymethyl-6-methyl-pyridin-3-ylmethyl]-amino}-biphenyl-2-sulfonic acid tert-butylamide

HRID 2373307ノート

反応式

HRID 2373307 の反応式
[C:1]([NH:5][S:6]([C:9]1[C:10]([C:15]2[CH:20]=[CH:19][C:18]([NH:21][CH2:22][C:23]3[CH:24]=[N:25][C:26]([CH3:32])=[C:27]([OH:31])[C:28]=3[CH2:29][OH:30])=[CH:17][CH:16]=2)=[CH:11][CH:12]=[CH:13][CH:14]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([C:41]#[N:42])[CH:36]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:1]([NH:5][S:6]([C:9]1[C:10]([C:15]2[CH:16]=[CH:17][C:18]([NH:21][CH2:22][C:23]3[CH:24]=[N:25][C:26]([CH3:32])=[C:27]([O:31][CH2:34][C:35]4[CH:40]=[CH:39][CH:38]=[C:37]([C:41]#[N:42])[CH:36]=4)[C:28]=3[CH2:29][OH:30])=[CH:19][CH:20]=2)=[CH:11][CH:12]=[CH:13][CH:14]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 97249Benzonitrile, 3-(bromomethyl)-HCID 598525284'-[(5-Hydroxy-4-hydroxymethyl-6-methyl-pyridin-3-ylmethyl)-amino]-biphenyl-2-sulfonic acid tert-butylamide

生成物 1

HCID 598525264'-{[5-(3-Cyano-benzyloxy)-4-hydroxymethyl-6-methyl-pyridin-3-ylmethyl]-amino}-biphenyl-2-sulfonic acid tert-butylamide収率 62.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 4′-[(5-hydroxy-4-hydroxymethyl-6-methyl-pyridin-3-ylmethyl)-amino]-biphenyl-2-sulfonic acid tert-butylamide (2) (190 mg, 0.42 mmol), α-bromo-m-tolunitrile (90 mg, 0.46 mmol) and potassium carbonate (177 mg, 1.28 mmol) in DMF (10 mL) were stirred at room temperature under nitrogen atmosphere overnight. The reaction mixture was evaporated to dryness, and the crude product was purified by column chromatography on silica gel using a gradient of dichloromethane:methyl alcohol (1:0 to 9:1) as eluant to give 4′-{[5-(3-cyano-benzyloxy)-4-hydroxymethyl-6-methyl-pyridin-3-ylmethyl]-amino}-biphenyl-2-sulfonic acid tert-butylamide (13) (149 mg, 62% yield) as a colorless solid.

後処理

  1. customThe reaction mixture was evaporated to dryness
  2. customthe crude product was purified by column chromatography on silica gel using a gradient of dichloromethane:methyl alcohol (1:0 to 9:1) as eluant

出典と根拠

ORDレコード
ord-859f3cbfa78847ad81fc0095e8ea2ecc
出典データセット
uspto-grants-2008_12
特許番号
US07459468B2

反応ノート

読み込み中…