Sodium Bicarbonate → HCID 10248891, compound

HRID 1271870Notes

Reaction equation

HRID 1271870 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][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=3)=[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][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=3)=[CH:25][C:19]=2[CH:18]=1)=[O:16]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 69490339HCID 69490339, compound

Product 1

HCID 10248891HCID 10248891, compoundYield 582.8%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 72 mg (0.151 mmol) of (2-{[5-(Pyridin-2-ylmethoxy)-benzo[b]thiophene-2-carbonyl]-amino}-phenyl)-carbamic acid tert-butyl ester (52) in 1.0 ml trifluoroacetic acid was stirred for 45 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 to yield 33 mg (0.88 mmol) 5-(Pyridin-2-ylmethoxy)-benzo[b]thiophene-2-carboxylic acid (2-amino-phenyl)-amide (51) as white solid, mp. 205–207° C.

Workup

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

Sources & evidence

ORD record
ord-df74571106d444bc9e46af0cb7312eb2
Source dataset
uspto-grants-2007_04
Patent number
US07208491B2

Reaction notes

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