Sulfuric Acid → 1-Amino-7-[4-(methylsulfonyl)phenyl][1]benzothieno[3,2-c]pyridine-4-carboxamide

HRID 1896529Notes

Reaction equation

HRID 1896529 reaction equation
COC1C=CC(C[NH:8][C:9]2[C:14]3[C:15]4[CH:21]=[CH:20][C:19]([C:22]5[CH:27]=[CH:26][C:25]([S:28]([CH3:31])(=[O:30])=[O:29])=[CH:24][CH:23]=5)=[CH:18][C:16]=4[S:17][C:13]=3[C:12]([C:32]#[N:33])=[CH:11][N:10]=2)=CC=1.[OH:36]S(O)(=O)=O.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O>[NH2:8][C:9]1[C:14]2[C:15]3[CH:21]=[CH:20][C:19]([C:22]4[CH:23]=[CH:24][C:25]([S:28]([CH3:31])(=[O:30])=[O:29])=[CH:26][CH:27]=4)=[CH:18][C:16]=3[S:17][C:13]=2[C:12]([C:32]([NH2:33])=[O:36])=[CH:11][N:10]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 62657Potassium Phosphate, TribasicHCID 59198486HCID 59198486, compound

Product 1

HCID 235819301-Amino-7-[4-(methylsulfonyl)phenyl][1]benzothieno[3,2-c]pyridine-4-carboxamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1-[(4-methoxybenzyl)amino]-7-[4-(methylsulfonyl)phenyl][1]benzothieno[3,2-c]pyridine-4-carbonitrile in conc. H2SO4 (45 equiv) was stirred at room temperature for 2 h and then poured into H2O. The mixture was neutralized with K3PO4, filtered, washed with H2O and dried. The crude product was purified by flash chromatography on silica gel, eluted with 10% MeOH in EtOAc to provide the title compound.

Workup

  1. filtrationfiltered
  2. washwashed with H2O
  3. customdried
  4. customThe crude product was purified by flash chromatography on silica gel
  5. washeluted with 10% MeOH in EtOAc

Sources & evidence

ORD record
ord-03221372fe624199acf2ed801e47aae4
Source dataset
uspto-grants-2013_08
Patent number
US08518964B2

Reaction notes

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