Trifluoroacetic acid → HCID 178485303, compound
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]([C:35]3[CH:40]=[CH:39][C:38]([C:41](=[O:44])[NH:42][CH3:43])=[CH:37][CH:36]=3)=[N:9]2)=CC=1.C(O)(C(F)(F)F)=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]([C:35]3[CH:36]=[CH:37][C:38]([C:41](=[O:44])[NH:42][CH3:43])=[CH:39][CH:40]=3)[C:11]=12Participants
3
Conditions
- Temperature
- 80 °C
Procedure
A 50 mL round-bottomed flask was charged with N-(4-(1-(4-methoxybenzyl)-3-(4-(methylcarbamoyl)phenyl)-1H-pyrazolo[3,4-b]pyridin-4-yloxy)-3-fluorophenyl)-1-methyl-2-oxopyrrolidine-3-carboxamide (10.8 mg, 0.0173 mmol) and CF3COOH (2 mL). The reaction mixture was stirred at 80° C. for 4 hours. Then the CF3COOH was removed under reduced pressure. The residue was purified by silica gel chromatography (DCM/7 M NH3 in MeOH from 50/1 to 10/1, v/v) to afford product (3.9 mg, 44.7%). LRMS (APCI pos): >99% purity, 254 nm, m/e 503 (M+1). 1H NMR (400 MHz, CD3OD) δ 8.35 (d, 1H), 8.10 (d, 2H), 7.83-7.90 (m, 3H), 7.40 (d, 1H), 7.32 (t, 1H), 6.40 (d, 1H), 3.44-3.60 (m, 3H), 2.92 (s, 3H), 2.90 (s, 3H), 2.28-2.51 (m, 2H).
Workup
- customThen the CF3COOH 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-ffb1351df1fe4fccae4f60b8ff5da952
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07723330B2
Reaction notes
Loading…