Sodium Bicarbonate → HCID 178491840, compound

HRID 750481Notes

Reaction equation

HRID 750481 reaction equation
Cl[C:2]1[N:7]=[C:6]2[NH:8][N:9]=[C:10]([C:11]3[C:16]([O:17][CH3:18])=[CH:15][CH:14]=[C:13]([F:19])[C:12]=3[F:20])[C:5]2=[CH:4][N:3]=1.C(=O)(O)[O-].[Na+].[CH3:26][S:27]([N:30]1[CH2:35][CH2:34][CH:33]([NH2:36])[CH2:32][CH2:31]1)(=[O:29])=[O:28]>CN(C=O)C>[F:20][C:12]1[C:13]([F:19])=[CH:14][CH:15]=[C:16]([O:17][CH3:18])[C:11]=1[C:10]1[C:5]2[C:6](=[N:7][C:2]([NH:36][CH:33]3[CH2:34][CH2:35][N:30]([S:27]([CH3:26])(=[O:29])=[O:28])[CH2:31][CH2:32]3)=[N:3][CH:4]=2)[NH:8][N:9]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 113558261-(Methanesulfonyl)piperidin-4-amineHCID 178491839HCID 178491839, compound

Product 1

HCID 178491840HCID 178491840, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of 6-chloro-3-(2,3-difluoro-6-methoxy-phenyl)-1H-pyrazolo[3,4-d]pyrimidine (Example 3, 148 mg, 0.50 mmol) in DMF (2.5 mL), sodium bicarbonate (100 mg) and 1-methanesulfonyl-piperidin-4-ylamine, 125 mg, 0.70 mmol) were added and the mixture was stirred at 100° C. for 4 hours. The solvent was removed under reduced pressure and the residue was treated with water. The solid was filtered and dried. Recrystallization from 2% MeOH/CH2Cl2 gave 92 mg off-white solid. 42%. MS (M+H)+, 439.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionthe residue was treated with water
  3. filtrationThe solid was filtered
  4. customdried
  5. customRecrystallization from 2% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-29aa85e7321343739e17285094874885
Source dataset
uspto-grants-2008_07
Patent number
US07405220B2

Reaction notes

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