Trifluoroacetic acid → HCID 178434453, compound

HRID 2241247Notes

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]([CH:27]5[CH2:31][CH2:30][NH:29][C:28]5=[O:32])=[O:26])=[CH:20][C:19]=4[F:33])=[C:11]3[C:10]([CH3:34])=[N:9]2)=CC=1.FC(F)(F)C(O)=O>>[F:33][C:19]1[CH:20]=[C:21]([NH:24][C:25]([CH:27]2[CH2:31][CH2:30][NH:29][C:28]2=[O:32])=[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]([CH3:34])[C:11]=12

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 68514543N-(4-(1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-4-yloxy)-3-fluorophenyl)-2-oxopyrrolidine-3-carboxamide

Product 1

HCID 178434453HCID 178434453, compoundYield 88.6%

Conditions

Temperature: 60 °C

Procedure

A 100 mL round-bottomed flask was charged with N-(4-(1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-4-yloxy)-3-fluorophenyl)-2-oxopyrrolidine-3-carboxamide (22.3 mg, 0.046 mmol) and 2,2,2-trifluoroacetic acid (259.7 mg, 2.28 mmol). The reaction mixture was stirred at 60° C. until LC-MS showed that the starting material was consumed (8 hour). The CF3COOH was removed under reduced pressure and the residue purified by column (Silica gel, DCM/7 M NH3 in MeOH from 50/1 to 10/1, v/v) to give the desired product (14.9 mg, 88.6%). HPLC: >99% purity, 1.91 min (254 nm); LRMS (APCI neg) m/e 368 (M−1). 1H NMR (400 MHz, CD3OD) δ 8.25 (d, J=5.6 Hz, 1H), 7.85 (dd, J=12.4, 2.4 Hz, 1H), 7.43 (m, 1H), 7.37 (t, J=8.8 Hz, 1H), 6.25 (dd, J=5.6, 0.8 Hz, 1H), 3.52-3.38 (m, 2H), 3.31 (m, 1H), 2.71 (s, 3H), 2.52-2.59 (m, 1H), 2.38-2.44 (m, 1H).

Workup

customwas consumed (8 hour)
customThe CF3COOH was removed under reduced pressure
customthe residue purified by column (Silica gel, DCM/7 M NH3 in MeOH from 50/1 to 10/1

Sources & evidence

ORD record: ord-976a9577370b4ca0b4904dd4b455d81b
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723330B2

Reaction notes

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