Trifluoroacetic acid → HCID 135968104, compound

HRID 2241288Notes

Reaction equation

COC1C=CC(C[N:8]2[C:12]3=[N:13][CH:14]=[CH:15][C:16]([O:17][C:18]4[CH:23]=[CH:22][C:21]([NH:24][C:25]([C:27]5[C:32](=[O:33])[N:31]([C:34]6[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=6)[N:30]=[CH:29][CH:28]=5)=[O:26])=[CH:20][C:19]=4[F:41])=[C:11]3[C:10]([C:42]3[CH:43]=[N:44][N:45](C(OC(C)(C)C)=O)[CH:46]=3)=[N:9]2)=CC=1.C(O)(C(F)(F)F)=O>>[NH:44]1[CH:43]=[C:42]([C:10]2[C:11]3[C:12](=[N:13][CH:14]=[CH:15][C:16]=3[O:17][C:18]3[CH:23]=[CH:22][C:21]([NH:24][C:25]([C:27]4[C:32](=[O:33])[N:31]([C:34]5[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=5)[N:30]=[CH:29][CH:28]=4)=[O:26])=[CH:20][C:19]=3[F:41])[NH:8][N:9]=2)[CH:46]=[N:45]1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 68513319HCID 68513319, compound

Product 1

HCID 135968104HCID 135968104, compoundYield 85%

Conditions

Temperature: 60 °C

Procedure

A 50 mL round-bottomed flask was charged with tert-butyl 4-(1-(4-methoxybenzyl)-4-(2-fluoro-4-(1-(4-fluorophenyl)-6-oxo-1,6-dihydropyridazine-5-carboxamido) phenoxy)-1H-pyrazolo[3,4-b]pyridin-3-yl)-1H-pyrazole-1-carboxylate (29.7 mg, 0.0398 mmol) and CF3COOH (5 mL). The reaction mixture was stirred at 60° C. for 4 hours. Then the solvent was removed and the residue was purified by silica gel chromatography (DCM/7 M NH3 in MeOH from 50/1 to 10/1, v/v) to give product (17.8 mg, 85.0%). LRMS (APCI pos): >99% purity, 254 nm, m/e 527 (M+1). 1H NMR (400 MHz, DMSO-d6) δ 13.65 (s, 1H), 13.0 (s, 1H), 11.74 (s, 1H), 8.38 (d, 1H), 8.32 (d, 1H), 8.27 (d, 1H), 8.22 (s, 1H), 8.01-8.12 (m, 2H), 7.69 (m, 2H), 7.61 (m, 2H), 7.42 (m, 2H), 6.32 (d, 1H).

Workup

customThen the solvent was removed
customthe residue was purified by silica gel chromatography (DCM/7 M NH3 in MeOH from 50/1 to 10/1

Sources & evidence

ORD record: ord-699fb82109b64d228b46e3e33e8d9860
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723330B2

Reaction notes

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