Trifluoroacetic acid → HCID 42598887, compound

HRID 1472799Notes

Reaction equation

C(O[C:6](=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:19]3[N:20]=[C:21]([NH:23][C:24]([CH:26]4[CH2:28][CH2:27]4)=[O:25])[N:22]=[C:18]3[CH:17]=[CH:16][CH:15]=2)=[CH:10][CH:9]=1)(C)(C)C.FC(F)(F)C(O)=O>>[CH3:6][NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:19]3[N:20]=[C:21]([NH:23][C:24]([CH:26]4[CH2:28][CH2:27]4)=[O:25])[N:22]=[C:18]3[CH:17]=[CH:16][CH:15]=2)=[CH:10][CH:9]=1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 42598422HCID 42598422, compound

Product 1

HCID 42598887HCID 42598887, compound

Procedure

To {4-[2-(cyclopropanecarbonyl-amino)-[1,2,4]triazolo[1,5-a]pyridin-5-yl]-phenyl}-carbamic acid tert-butyl ester (WW-119) (0.05 g, 0.123 mmol), trifluoroacetic acid (1 mL) was added and the solution was stirred for 2 h. The solvent was removed under reduced pressure and the crude product was purified by preparatory HPLC. LCMS method: 1, RT: 3.62 min; MI: 308 [M+1]. NMR 1H (DMSO) 0.80-0.83 (m, 4H), 1.93 (brs, 1H), 2.73 (s, 3H), 6.63 (d, 2H), 7.16 (d, 1H), 7.42 (d, 1H), 7.57 (t, 1H), 8.01 (d, 2H).

Workup

customThe solvent was removed under reduced pressure
customthe crude product was purified by preparatory HPLC

Sources & evidence

ORD record: ord-87a5b7488e0e4cf9b875f957ee065f9d
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09012633B2

Reaction notes

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