Trifluoroacetic acid → 3-(3-Fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenylamino)propanoic acid

HRID 1177563Notes

Reaction equation

FC(F)(F)C(O)=O.[F:8][C:9]1[CH:10]=[C:11]([NH:33][CH2:34][CH2:35][C:36]([O:38]C(C)(C)C)=[O:37])[CH:12]=[CH:13][C:14]=1[C:15]1[S:16][C:17]2[C:22]([N:23]=1)=[CH:21][CH:20]=[C:19]([C:24]1([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:26][CH2:25]1)[N:18]=2>C(Cl)Cl>[F:8][C:9]1[CH:10]=[C:11]([NH:33][CH2:34][CH2:35][C:36]([OH:38])=[O:37])[CH:12]=[CH:13][C:14]=1[C:15]1[S:16][C:17]2[C:22]([N:23]=1)=[CH:21][CH:20]=[C:19]([C:24]1([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:25][CH2:26]1)[N:18]=2

Participants

Conditions

Temperature: 25 °C

Procedure

2,2,2-Trifluoroacetic acid (360 μl, 4.67 mmol) was added to a solution of tert-butyl 3-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenylamino)propanoate (46.5 mg, 0.095 mmol) in DCM (2.0 mL) at 25° C., and the resulting solution was stirred at 25° C. for 19 h. The reaction solution was then concentrated in vacuo, and the residue was taken up in DMSO (2.0 mL) and purified by rpHPLC (10-100% CH3CN/water+0.1% TFA) to provide 3-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenylamino)propanoic acid as a yellow solid. MS (ESI) m/z: Calculated: 433.1; Observed: 434.0 (M++1).

Workup

concentrationThe reaction solution was then concentrated in vacuo
custompurified by rpHPLC (10-100% CH3CN/water+0.1% TFA)

Sources & evidence

ORD record: ord-d0274c306fcc4982a756931ec6c82743
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842685B2

Reaction notes

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