Sodium Bicarbonate → HCID 66584380, compound

HRID 334376Notes

Reaction equation

[NH2:1][C:2]1[N:7]2[N:8]=[CH:9][C:10]([C:11]3[CH:12]=[N:13][N:14]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH:15]=3)=[C:6]2[N:5]=[C:4]([CH:22]2[CH2:27][CH2:26][C:25]([CH2:29][OH:30])([OH:28])[CH2:24][CH2:23]2)[C:3]=1SC.[C:33]([O-])(O)=O.[Na+].O[O:39][S:40]([O-:42])=O.[K+]>CO.O>[NH2:1][C:2]1[N:7]2[N:8]=[CH:9][C:10]([C:11]3[CH:12]=[N:13][N:14]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH:15]=3)=[C:6]2[N:5]=[C:4]([CH:22]2[CH2:27][CH2:26][C:25]([CH2:29][OH:30])([OH:28])[CH2:24][CH2:23]2)[C:3]=1[S:40]([CH3:33])(=[O:42])=[O:39]

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of 4-(7-amino-6-(methylthio)-3-(1-phenyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-1-(hydroxymethyl)cyclohexanol (32.0 mg, 0.0710 mmol) in a mixed solvent of MeOH/H2O (2/0.5 mL) was added NaHCO3 (23.8 mg, 0.284 mmol), followed by Oxone (87.3 mg, 0.142 mmol) at rt. The resulting mixture was stirred at 40° C. for 2.5 h. The reaction mixture was filtered and washed with DMF and MeOH. The combined filtrate was concentrated and purified by a reverse phase HPLC to afford 4-(7-amino-6-(methylsulfonyl)-3-(1-phenyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-1-(hydroxymethyl)cyclohexanol as a white solid (6.4 mg). HPLC-MS TR=4.08 min (UV 254 nm, 10 min method); mass calculated for formula C23H26N6O4S 482.2, observed LCMS m/z 483 (M+H).

Workup

filtrationThe reaction mixture was filtered
washwashed with DMF and MeOH
concentrationThe combined filtrate was concentrated
custompurified by a reverse phase HPLC

Sources & evidence

ORD record: ord-7f45d9c47ad34ecbae2cbb2dd42c7a7d
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883801B2

Reaction notes

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