Hydrochloric Acid → 4-(3-Fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenyl)butanoic acid

HRID 1177610Notes

Reaction equation

HRID 1177610 reaction equation
Cl.[F:2][C:3]1[CH:4]=[C:5]([CH2:27][CH2:28][CH:29](C(OCC)=O)[C:30]([O:32]CC)=[O:31])[CH:6]=[CH:7][C:8]=1[C:9]1[S:10][C:11]2[C:16]([N:17]=1)=[CH:15][CH:14]=[C:13]([C:18]1([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:20][CH2:19]1)[N:12]=2>>[F:2][C:3]1[CH:4]=[C:5]([CH2:27][CH2:28][CH2:29][C:30]([OH:32])=[O:31])[CH:6]=[CH:7][C:8]=1[C:9]1[S:10][C:11]2[C:16]([N:17]=1)=[CH:15][CH:14]=[C:13]([C:18]1([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:20][CH2:19]1)[N:12]=2

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 67111704Diethyl 2-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenethyl)malonate

Product 1

HCID 446004844-(3-Fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenyl)butanoic acid

Conditions

Temperature
120 °C

Procedure

In reactor bottle, hydrochloric acid, 5N aq. (3 mL) was added to diethyl 2-(2-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenyl)ethyl)malonate (0.257 g, 0.48 mmol), and the mixture heated to 120° C. for 6 h. The crude reaction mixture was concentrated in vacuo and purified by silica gel chromatography to afford 4-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenyl)butanoic acid. MS (ESI) m/z: calculated: 432.1; Observed: 433.0 (M++1).

Workup

  1. customThe crude reaction mixture
  2. concentrationwas concentrated in vacuo
  3. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-f0818982d1fa4a8091c738c4baff3f4c
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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