HCID 73335541, compound → HCID 136252340, compound

HRID 710634Notes

Reaction equation

HRID 710634 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[CH2:15][CH2:14][CH2:13][N:12]([C:17](=[O:32])[CH2:18][N:19]4[C:23]5=[N:24][CH:25]=[CH:26][CH:27]=[C:22]5[C:21]([C:28]([F:31])([F:30])[F:29])=[N:20]4)[C:11]=3[CH:10]=[N:9]2)=[CH:4][CH:3]=1>CO.O=[Pt]=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[CH2:15][CH2:14][CH2:13][N:12]([C:17](=[O:32])[CH2:18][N:19]4[C:23]5[NH:24][CH2:25][CH2:26][CH2:27][C:22]=5[C:21]([C:28]([F:29])([F:31])[F:30])=[N:20]4)[C:11]=3[CH:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 73335541HCID 73335541, compound

Product 1

HCID 136252340HCID 136252340, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

1-[1-(4-Fluorophenyl)-6,7-dihydro-5H-pyrazolo[4,3-b]pyridin-4-yl]-2-[3-(trifluoromethyl)pyrazolo[3,4-b]pyridin-1-yl]ethanone (22.2 mg, 0.05 mmol) prepared above was dissolved in 1 mL of methanol and treated with ˜20 mg of PtO2 in a septum-capped vial. The vial was purged and filled with hydrogen gas twice and then placed under a hydrogen atmosphere (balloon) and stirred overnight. The slurry was filtered and the filtrate purified by reverse phase HPLC (C18 column, acetonitrile-H2O with 0.1% TFA as eluent) to provide the title compound (solution was neutralized and extracted to provide the free base) as a white solid (13 mg, 60%). 1H NMR (400 MHz, CDCl3, mixture of rotamers) δ 8.36 (s, 0.85H), 7.71 (s, 0.15H), 7.43-7.49 (m, 2H), 7.14-7.19 (m, 2H), 5.15 (s, 0.3H), 5.00 (s, 1.7H), 4.29 (br s, 1H), 3.88-3.93 (m, 2H), 3.29 (m, 2H), 2.85 (t, J=6.3 Hz, 2H), 2.63 (t, J=6.2 Hz, 2H), 2.09 (m, 2H), 1.85 (m, 2H); MS: (ES) m/z calculated for C21H21F4N6O [M+H]+ 449.1, found 449.1.

Workup

  1. customThe vial was purged
  2. additionfilled with hydrogen gas twice
  3. filtrationThe slurry was filtered
  4. customthe filtrate purified by reverse phase HPLC (C18 column, acetonitrile-H2O with 0.1% TFA as eluent)

Sources & evidence

ORD record
ord-2c7548eb92ca4244b14c13e0a59eff61
Source dataset
uspto-grants-2015_11
Patent number
US09181241B2

Reaction notes

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