Potassium Carbonate → HCID 21897897, compound

HRID 1864154Notes

Reaction equation

HRID 1864154 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([C:11]3[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][CH:12]=3)[N:9]=[CH:10][C:3]=12.[C:21]([O:25][C:26]([N:28]1[CH2:33][CH2:32][CH:31]([SH:34])[CH2:30][CH2:29]1)=[O:27])([CH3:24])([CH3:23])[CH3:22].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:21]([O:25][C:26]([N:28]1[CH2:33][CH2:32][CH:31]([S:34][C:2]2[N:7]=[CH:6][N:5]=[C:4]3[N:8]([C:11]4[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][CH:12]=4)[N:9]=[CH:10][C:3]=23)[CH2:30][CH2:29]1)=[O:27])([CH3:24])([CH3:22])[CH3:23]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 218974474-Chloro-1-[4-(methanesulfonyl)phenyl]-1H-pyrazolo[3,4-d]pyrimidineHCID 21906090tert-Butyl 4-sulfanylpiperidine-1-carboxylate

Product 1

HCID 21897897HCID 21897897, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Chloro-1-(4-methanesulfonyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidine (1.23 mmol, 250 mg), 4-mercapto-piperidine-1-carboxylic acid tert-butyl ester (1.23 mmol, 268 mg) and potassium carbonate (1.4 mmol, 203 mg) were dissolved in DMF (10 mL) and stirred for 60 minutes at room temperature. Its progress was followed by thin layer chromatography and LCMS. The reaction mixture was quenched with water followed by an extraction with ethylacetate. Removal of organic solvents in vacuo and purification by column chromatography provided compound A102 as a white solid (264 mg, 66%). 1H NMR (400MHz, CDCl3) δ (ppm): 8.83 (s, 1H); 8.61 (d, 2H); 8.24 (s, 1H); 8.11 (d, 2H); 4.42 (h, 1H); 4.00 (m, 2H); 3.20 (m, 2H); 3.15 (s, 3H); 2.19 (m, 2H); 1.77 (m, 2H); 1.46 (s, 9H). LCMS (ESI), m/z 490.3 (MH+, 100%)

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionfollowed by an extraction with ethylacetate
  3. customRemoval of organic solvents
  4. customin vacuo and purification by column chromatography

Sources & evidence

ORD record
ord-2191a69b29d0456e85eef6f8dcf22132
Source dataset
uspto-grants-2009_12
Patent number
US07625906B2

Reaction notes

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