Hydrochloric Acid → 4'-[(5-Hydroxy-4-hydroxymethyl-6-methyl-pyridin-3-ylmethyl)-amino]-biphenyl-2-sulfonic acid amide

HRID 2373303Notes

Reaction equation

HRID 2373303 reaction equation
Cl.C([NH:6][S:7]([C:10]1[C:11]([C:16]2[CH:21]=[CH:20][C:19]([NH:22][CH2:23][C:24]3[CH:25]=[N:26][C:27]([CH3:33])=[C:28]([OH:32])[C:29]=3[CH2:30][OH:31])=[CH:18][CH:17]=2)=[CH:12][CH:13]=[CH:14][CH:15]=1)(=[O:9])=[O:8])(C)(C)C>CO>[OH:32][C:28]1[C:29]([CH2:30][OH:31])=[C:24]([CH2:23][NH:22][C:19]2[CH:18]=[CH:17][C:16]([C:11]3[C:10]([S:7]([NH2:6])(=[O:9])=[O:8])=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:21][CH:20]=2)[CH:25]=[N:26][C:27]=1[CH3:33]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 598525284'-[(5-Hydroxy-4-hydroxymethyl-6-methyl-pyridin-3-ylmethyl)-amino]-biphenyl-2-sulfonic acid tert-butylamide

Product 1

HCID 598525314'-[(5-Hydroxy-4-hydroxymethyl-6-methyl-pyridin-3-ylmethyl)-amino]-biphenyl-2-sulfonic acid amideYield 96.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Hydrogen chloride gas was bubbled into a suspension of 4′-[(5-hydroxy-4-hydroxymethyl-6-methyl-pyridin-3-ylmethyl)-amino]-biphenyl-2-sulfonic acid tert-butylamide (2) (160 mg, 0.36 mmol) in methyl alcohol (20 mL) at 0° C. for 10 minutes. The solvent was evaporated and the products were purified on a silica gel column using a mixture of methyl alcohol:dichloromethane (1:9) as eluant to give 4′-[(5-hydroxy-4-hydroxymethyl-6-methyl-pyridin-3-ylmethyl)-amino]-biphenyl-2-sulfonic acid amide (3) (139 mg, 25% yield).

Workup

  1. customThe solvent was evaporated
  2. customthe products were purified on a silica gel column
  3. additiona mixture of methyl alcohol:dichloromethane (1:9) as eluant

Sources & evidence

ORD record
ord-55accf8080394f81808fe7c802b31586
Source dataset
uspto-grants-2008_12
Patent number
US07459468B2

Reaction notes

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