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

HRID 2373307노트

반응식

HRID 2373307 반응식
[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]

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-859f3cbfa78847ad81fc0095e8ea2ecc
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07459468B2

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