Trifluoroacetic acid → HCID 178434455, compound

HRID 2241251Notes

Reaction equation

HRID 2241251 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][N:29]([CH3:32])[C:28]5=[O:33])=[O:26])=[CH:20][C:19]=4[F:34])=[C:11]3[C:10]([CH3:35])=[N:9]2)=CC=1.FC(F)(F)C(O)=O>>[F:34][C:19]1[CH:20]=[C:21]([NH:24][C:25]([CH:27]2[CH2:31][CH2:30][N:29]([CH3:32])[C:28]2=[O:33])=[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]([CH3:35])[C:11]=12

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68513401N-(4-(1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-4-yloxy)-3-fluorophenyl)-1-methyl-2-oxopyrrolidine-3-carboxamide

Product 1

HCID 178434455HCID 178434455, compoundYield 90.5%

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)-1-methyl-2-oxopyrrolidine-3-carboxamide (14.8 mg, 0.0294 mmol) and 2,2,2-trifluoroacetic acid (335 mg, 2.94 mmol). The reaction mixture was stirred at 60° C. until LC-MS showed that the starting material was consumed. The CF3COOH was removed under reduced pressure and purified the resulting residue was purified by silica gel chromatography (DCM/7 M NH3 in MeOH from 50/1 to 10/1, v/v) to give the desired product (10.2 mg, 90.5%). LRMS (APCI neg) m/e 382 (M−1). 1H NMR (400 MHz, CD3OD) δ 8.25 (d, J=6.0 Hz, 1H), 7.85 (dd, J=12.8, 2.4 Hz, 1H), 7.42 (m, 1H), 7.37 (m, 1H), 6.25 (m, 1H), 3.44-3.59 (m, 2H), 3.31 (m, 1H), 2.90 (s, 3H), 2.71 (s, 3H), 2.44-2.49 (m, 1H), 2.30-2.37 (m, 1H).

Workup

  1. customwas consumed
  2. customThe CF3COOH was removed under reduced pressure
  3. custompurified the resulting residue
  4. customwas purified by silica gel chromatography (DCM/7 M NH3 in MeOH from 50/1 to 10/1

Sources & evidence

ORD record
ord-b28259de20cc437c89be19054c7d3b90
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

Loading…