HCID 68509812, compound → HCID 178434447, compound

HRID 2241243Notes

Reaction equation

[CH:1]1([CH2:4][NH:5][C:6]2[N:11]([CH3:12])[C:10](=[O:13])[C:9]([C:14]3[CH:19]=[CH:18][C:17]([O:20][C:21]4[CH:26]=[CH:25][N:24]=[C:23]5[N:27](CC6C=CC(OC)=CC=6)[N:28]=[C:29]([CH3:30])[C:22]=45)=[C:16]([F:40])[CH:15]=3)=[CH:8][N:7]=2)[CH2:3][CH2:2]1>C(O)(C(F)(F)F)=O>[CH:1]1([CH2:4][NH:5][C:6]2[N:11]([CH3:12])[C:10](=[O:13])[C:9]([C:14]3[CH:19]=[CH:18][C:17]([O:20][C:21]4[CH:26]=[CH:25][N:24]=[C:23]5[NH:27][N:28]=[C:29]([CH3:30])[C:22]=45)=[C:16]([F:40])[CH:15]=3)=[CH:8][N:7]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a 15 mL capacity reaction tube was added 2-(cyclopropylmethylamino)-5-(3-fluoro-4-(1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-4-yloxy)phenyl)-3-methylpyrimidin-4(3H)-one (23.8 mg, 0.044 mmol) and the solids were dissolved in TFA (0.5 mL, excess). The reaction mixture was stirred at 80° C. for 1 hour in a sealed tube. The excess solvent was evaporated and the crude residue was purified by silica gel chromatography (Biotage 12M) loading with EtOAc and eluting with 3% MeOH/EtOAc to give the title compound as pink solid (8.5 mg, 46%). LRMS (APCI pos) m/e 421.3 (M+1). 1H NMR (400 MHz, DMSO-d6) δ 13.29 (s, 1H), 8.27 (d, J=5.5 Hz, 1H), 8.10 (s, 1H), 7.85 (br d, 1H), 7.65 (d, J=8.6 Hz, 1H), 7.53 (t, J=5.5 Hz, 1H), 7.43 (t, J=8.6 Hz, 1H), 6.23 (d, J=5.5 Hz, 1H), 3.38 (s, 3H), 3.28 (t, J=6.2 Hz, 2H), 2.63 (s, 3H), 1.17 (t, J=7.2 Hz, 1H), 0.46 (q, J=6.8 Hz, 2H), 0.28 (q, J=4.9 Hz, 2H).

Workup

customTo a 15 mL capacity reaction tube
customThe excess solvent was evaporated
customthe crude residue was purified by silica gel chromatography (Biotage 12M) loading with EtOAc
washeluting with 3% MeOH/EtOAc

Sources & evidence

ORD record: ord-ec129d6eccec46d79dbce974429bd51c
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723330B2

Reaction notes

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