Trifluoroacetic acid → HCID 44599852, compound

HRID 1177574Notes

Reaction equation

FC(F)(F)C(O)=O.[F:8][C:9]1[CH:10]=[C:11]([CH2:33][NH:34][C@@H:35]([CH3:43])[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]([CH2:33][NH:34][C@@H:35]([CH3:43])[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

Trifluoroacetic acid (1.0 mL, 12.98 mmol) was added to a solution of (S)-tert-butyl 2-((3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenyl)methylamino)propanoate (140.6 mg, 0.279 mmol) in DCM (2.1 mL) at 25° C., and the resulting mixture was stirred at 25° C. for 16 h. The reaction mixture was then concentrated in vacuo and the brown residue was taken up in DMSO (2.0 mL) and purified by rpHPLC (10-100% CH3CN/water+0.1% TFA) to provide (S)-2-((3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenyl)methylamino)-propanoic acid as a light yellow solid. MS (ESI) m/z: Calculated: 447.1; Observed: 448.2 (M++1).

Workup

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

Sources & evidence

ORD record: ord-0398e7073274426098a99164b13996c0
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842685B2

Reaction notes

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