2-Ethyl-1-butanol → 4-[1-(4-Methanesulfonyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy]-piperidine-1-carboxylic acid 2-ethyl-butyl ester

HRID 1864106Notes

Reaction equation

HRID 1864106 reaction equation
N1([C:6](N2C=CN=C2)=[O:7])C=CN=C1.[CH2:13]([CH:15]([CH2:18][CH3:19])[CH2:16][OH:17])[CH3:14].[CH3:20][S:21]([C:24]1[CH:29]=[CH:28][C:27]([N:30]2[C:34]3=[N:35][CH:36]=[N:37][C:38]([O:39][CH:40]4[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]4)=[C:33]3[CH:32]=[N:31]2)=[CH:26][CH:25]=1)(=[O:23])=[O:22].C(N(CC)CC)C>CS(C)=O>[CH2:13]([CH:15]([CH2:18][CH3:19])[CH2:16][O:17][C:6]([N:43]1[CH2:44][CH2:45][CH:40]([O:39][C:38]2[N:37]=[CH:36][N:35]=[C:34]3[N:30]([C:27]4[CH:28]=[CH:29][C:24]([S:21]([CH3:20])(=[O:22])=[O:23])=[CH:25][CH:26]=4)[N:31]=[CH:32][C:33]=23)[CH2:41][CH2:42]1)=[O:7])[CH3:14]

Participants

6

Reactant 4

HCID 73582-Ethyl-1-butanolHCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 113608021-(4-methanesulfonyl-phenyl)-4-(piperidin-4-yloxy)-1H-pyrazolo[3,4-d]pyrimidine

Product 1

HCID 218977034-[1-(4-Methanesulfonyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy]-piperidine-1-carboxylic acid 2-ethyl-butyl esterYield 44.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Di-imidazol-1-yl-methanone (0.51 mmol, 83 mg), and 2-ethyl-butan-1-ol (0.51 mmol, 52 mg) were dissolved in DMSO (1 mL) and stirred for 30 minutes at room temperature. Then, 1-(4-methanesulfonyl-phenyl)-4-(piperidin-4-yloxy)-1H-pyrazolo[3,4-d]pyrimidine (0.17 mmol, 70 mg) and triethylamine (0.51 mmol, 72 μL) were added and heated in a microwave at 120° C. for 6 minutes. The progress of the reaction was monitored by LCMS. The reaction mixture was quenched with water and the product was extracted with ethylacetate. Removal of organic solvents in vacuo and purification by HPLC provided Compound A119 as a white solid (38 mg, 36%). Exact mass calculated for C24H31N5O5S 501.60, found 502.3 (MH+).

Workup

  1. temperatureheated in a microwave at 120° C. for 6 minutes
  2. customThe reaction mixture was quenched with water
  3. extractionthe product was extracted with ethylacetate
  4. customRemoval of organic solvents
  5. customin vacuo and purification by HPLC

Sources & evidence

ORD record
ord-703d287eb6da4522bb3fa769ee2a9e7b
Source dataset
uspto-grants-2009_12
Patent number
US07625906B2

Reaction notes

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