Sodium Carbonate → HCID 57964918, compound

HRID 1931675Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:18]3=[N:19][CH:20]=[N:21][C:22](Cl)=[C:17]3[CH:16]=[N:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH:24][C:25]1[CH:30]=[CH:29][C:28]([NH:31][S:32]([CH3:35])(=[O:34])=[O:33])=[C:27]([CH3:36])[CH:26]=1.C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:18]3=[N:19][CH:20]=[N:21][C:22]([O:24][C:25]4[CH:30]=[CH:29][C:28]([NH:31][S:32]([CH3:35])(=[O:34])=[O:33])=[C:27]([CH3:36])[CH:26]=4)=[C:17]3[CH:16]=[N:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 160 °C

Procedure

A mixture of 4-(4-chloro-pyrazolo[3,4-d]pyrimidin-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (Intermediate 19; 25 mg, 0.075 mmol), N-(4-hydroxy-2-methyl-phenyl)methanesulfonamide (ChemBridge Corporation, San Diego, Calif., USA; 15 mg, 0.075 mmol), and potassium carbonate (27 mg, 0.2 mmol) in dimethylformamide was heated in the microwave oven at 160° C. for 10 min. Saturated sodium carbonate solution was added to the reaction mixture and the precipitate was filtered through a silica plug, washing with methanol. The solvent was removed and the residue was purified by HPLC to afford 4-[4-(4-methanesulfonylamino-3-methyl-phenoxy)pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (12 mg, 33%) as an off white solid. Mass Spec MH+=503.

Workup

filtrationthe precipitate was filtered through a silica plug
washwashing with methanol
customThe solvent was removed
customthe residue was purified by HPLC

Sources & evidence

ORD record: ord-724739494b584e54885f4daf352dd5a9
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188098B2

Reaction notes

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