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

HRID 2373307Notes

Reaction equation

HRID 2373307 reaction equation
[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]

Participants

5

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-859f3cbfa78847ad81fc0095e8ea2ecc
Source dataset
uspto-grants-2008_12
Patent number
US07459468B2

Reaction notes

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