1-Pentanol → HCID 57496300, compound

HRID 1958375Notes

Reaction equation

HRID 1958375 reaction equation
N1([C:6](N2C=CN=C2)=[O:7])C=CN=C1.[CH2:13]([OH:18])[CH2:14][CH2:15][CH2:16][CH3:17].[CH3:19][S:20]([C:23]1[CH:28]=[CH:27][C:26]([N:29]2[C:33]3=[N:34][CH:35]=[N:36][C:37]([O:38][CH:39]4[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]4)=[C:32]3[CH:31]=[N:30]2)=[CH:25][CH:24]=1)(=[O:22])=[O:21].C(N(CC)CC)C>CS(C)=O>[CH2:13]([O:18][C:6]([N:42]1[CH2:43][CH2:44][CH:39]([O:38][C:37]2[N:36]=[CH:35][N:34]=[C:33]3[N:29]([C:26]4[CH:27]=[CH:28][C:23]([S:20]([CH3:19])(=[O:21])=[O:22])=[CH:24][CH:25]=4)[N:30]=[CH:31][C:32]=23)[CH2:40][CH2:41]1)=[O:7])[CH2:14][CH2:15][CH2:16][CH3:17]

Participants

6

Reactant 4

HCID 62761-PentanolHCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 113608021-(4-methanesulfonyl-phenyl)-4-(piperidin-4-yloxy)-1H-pyrazolo[3,4-d]pyrimidine

Product 1

HCID 57496300HCID 57496300, compoundYield 39.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Di-imidazol-1-yl-methanone (0.51 mmol, 83 mg), and n-pentanol (0.51 mmol, 56 μL) 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 A117 as a white solid (33 mg, 32%). Exact mass calculated for C23H29N5O5S 487.57, found 488.20 (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-c92b468e8a6a45e6b904bc65922dab58
Source dataset
uspto-grants-2013_04
Patent number
US08410119B2

Reaction notes

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