Triethylamine → 4-[1-(4-Methanesulfonyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy]-piperidine-1-carboxylic acid cyclopentylmethyl ester

HRID 1864107Notes

Reaction equation

HRID 1864107 reaction equation
N1([C:6](N2C=CN=C2)=[O:7])C=CN=C1.[CH:13]1([CH2:18][OH:19])[CH2:17][CH2:16][CH2:15][CH2:14]1.[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>[CH:13]1([CH2:18][O:19][C:6]([N:43]2[CH2:44][CH2:45][CH:40]([O:39][C:38]3[N:37]=[CH:36][N:35]=[C:34]4[N:30]([C:27]5[CH:28]=[CH:29][C:24]([S:21]([CH3:20])(=[O:22])=[O:23])=[CH:25][CH:26]=5)[N:31]=[CH:32][C:33]=34)[CH2:41][CH2:42]2)=[O:7])[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 77195CyclopentanemethanolHCID 113608021-(4-methanesulfonyl-phenyl)-4-(piperidin-4-yloxy)-1H-pyrazolo[3,4-d]pyrimidine

Product 1

HCID 218978094-[1-(4-Methanesulfonyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy]-piperidine-1-carboxylic acid cyclopentylmethyl esterYield 35.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Di-imidazol-1-yl-methanone (0.51 mmol, 83 mg), and cyclopentyl-methanol (0.51 mmol, 51 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 A120 as a white solid (30 mg, 29%). Exact mass calculated for C24H29N5O5S 499.58, found 500.4 (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-bfc542202c7e416393b665c1382a8704
Source dataset
uspto-grants-2009_12
Patent number
US07625906B2

Reaction notes

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