Trifluoroacetic acid → HCID 135939673, compound

HRID 2241293Notes

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:28](=[O:40])[N:29]([C:33]6[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=6)[N:30]=[CH:31][CH:32]=5)=[O:26])=[CH:20][C:19]=4[F:41])=[C:11]3[C:10]([C:42]3[CH:43]=[N:44][N:45]([CH3:47])[CH:46]=3)=[N:9]2)=CC=1.C(O)(C(F)(F)F)=O>>[F:41][C:19]1[CH:20]=[C:21]([NH:24][C:25]([C:27]2[C:28](=[O:40])[N:29]([C:33]3[CH:34]=[CH:35][C:36]([F:39])=[CH:37][CH:38]=3)[N:30]=[CH:31][CH:32]=2)=[O:26])[CH:22]=[CH:23][C:18]=1[O:17][C:16]1[CH:15]=[CH:14][N:13]=[C:12]2[NH:8][N:9]=[C:10]([C:42]3[CH:43]=[N:44][N:45]([CH3:47])[CH:46]=3)[C:11]=12

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 68512288HCID 68512288, compound

Product 1

HCID 135939673HCID 135939673, compoundYield 58.1%

Conditions

Temperature: 60 °C

Procedure

A 50 mL round-bottomed flask was charged N-(4-(1-(4-methoxybenzyl)-3-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-yloxy)-3-fluorophenyl)-2-(4-fluorophenyl)-3-oxo-2,3-dihydropyridazine-4-carboxamide (23.8 mg, 0.0360 mmol) and CF3COOH (5 mL). The reaction mixture was stirred at 60° C. until LC-MS showed that the starting material had been consumed (overnight). The solvent was removed under reduced pressure 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 (11.3 mg, 58%). LRMS (APCI pos): >99% purity, 254 nm, m/e 541 (M+1). 1H NMR (400 MHz, DMSO-d6) δ 13.66 (s, 1H), 11.72 (s, 1H), 8.38 (d, 1H), 8.31 (d, 1H), 8.27 (d, 1H), 8.18 (s, 1H), 8.06 (dd, 1H), 7.96 (s, 1H), 7.69 (m, 2H), 7.60 (m, 2H), 7.42 (m, 2H), 6.31 (d, 1H), 3.89 (s, 3H).

Workup

customhad been consumed (overnight)
customThe solvent was removed under reduced pressure
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-9ed7affe11fd4d25a0d3b386395dbc56
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723330B2

Reaction notes

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