Sodium Bicarbonate → HCID 10089559, compound

HRID 1271846Notes

Reaction equation

HRID 1271846 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15]([C:17]1[S:21][C:20]2[CH:22]=[CH:23][C:24]([O:26][CH2:27][CH2:28][N:29]([CH3:31])[CH3:30])=[CH:25][C:19]=2[CH:18]=1)=[O:16])(C)(C)C.C(=O)(O)[O-].[Na+]>FC(F)(F)C(O)=O>[NH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15]([C:17]1[S:21][C:20]2[CH:22]=[CH:23][C:24]([O:26][CH2:27][CH2:28][N:29]([CH3:31])[CH3:30])=[CH:25][C:19]=2[CH:18]=1)=[O:16]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 69489634HCID 69489634, compound

Product 1

HCID 10089559HCID 10089559, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 72 mg (0.158 mmol) (2-{[5-(2-Dimethylamino-ethoxy)-benzo[b]thiophene-2-carbonyl]-amino}-phenyl)-carbamic acid tert-butyl ester (5) in 1.0 ml trifluoroacetic acid was stirred for 60 min at room temperature and then added to an aqueous solution of sodium bicarbonate. After extraction with ethyl acetate and removal of the solvent the residue was recrystallized from ethyl acetate/diethyl ether to yield 35 mg (0.10 mmol) 5-(2-Dimethylamino-ethoxy)-benzo[b]thiophene-2-carboxylic acid (2-amino-phenyl)-amide (1) as a yellow solid, mp. 191–193° C.

Workup

  1. extractionAfter extraction
  2. customwith ethyl acetate and removal of the solvent the residue
  3. customwas recrystallized from ethyl acetate/diethyl ether

Sources & evidence

ORD record
ord-d2f6858cf02b45fb85e969b5246bb9fc
Source dataset
uspto-grants-2007_04
Patent number
US07208491B2

Reaction notes

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