Hydrochloric Acid → 1-(6-Chloro-benzo[b]thiophen-2-ylmethyl)-5-(2-methoxy-ethoxy)-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid

HRID 2250447Notes

Reaction equation

[Li+].[OH-].C([O:5][C:6]([C:8]1[N:21]([CH2:22][C:23]2[S:27][C:26]3[CH:28]=[C:29]([Cl:32])[CH:30]=[CH:31][C:25]=3[CH:24]=2)[C:11]2=[CH:12][N:13]=[C:14]([O:16][CH2:17][CH2:18][O:19][CH3:20])[CH:15]=[C:10]2[CH:9]=1)=[O:7])C.Cl>O.C1COCC1.CO>[Cl:32][C:29]1[CH:30]=[CH:31][C:25]2[CH:24]=[C:23]([CH2:22][N:21]3[C:11]4=[CH:12][N:13]=[C:14]([O:16][CH2:17][CH2:18][O:19][CH3:20])[CH:15]=[C:10]4[CH:9]=[C:8]3[C:6]([OH:7])=[O:5])[S:27][C:26]=2[CH:28]=1

Participants

Conditions

Temperature: 50 °C

Procedure

8 mL of a 1M LiOH solution in water were added to solution of 890 mg (2 mmol) 1-(6-Chloro-benzo[b]thiophen-2-ylmethyl)-5-(2-methoxy-ethoxy)-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid ethyl ester in 30 mL THF and 15 mL MeOH and the mixture was stirred for 1 h at 50° C. 16 mL of 1N HCl were added, the organic solvent removed in vacuo and the residue extracted with ethyl acetate. The organic phase was dried over MgSO4. After filtration the solvent was evaporated yielding the desired product. Yield: 810 mg.

Workup

customthe organic solvent removed in vacuo
extractionthe residue extracted with ethyl acetate
dry with materialThe organic phase was dried over MgSO4
filtrationAfter filtration the solvent
customwas evaporated

Sources & evidence

ORD record: ord-dc4a66ec97444ac8ab1e15d98774a983
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07317027B2

Reaction notes

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