Triethylamine → HCID 21897857, compound

HRID 1958376Notes

Reaction equation

HRID 1958376 reaction equation
N1([C:6](N2C=CN=C2)=[O:7])C=CN=C1.[CH3:13][CH2:14][CH:15]([OH:18])[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>[CH2:14]([CH:15]([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])[CH2:16][CH3:17])[CH3:13]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 114283-PentanolHCID 682631,1'-CarbonyldiimidazoleHCID 113608021-(4-methanesulfonyl-phenyl)-4-(piperidin-4-yloxy)-1H-pyrazolo[3,4-d]pyrimidine

Product 1

HCID 21897857HCID 21897857, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Di-imidazol-1-yl-methanone (0.51 mmol, 83 mg), and pentan-3-ol (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 A118 as a white solid (14 mg, 14%). 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
  6. customprovided Compound

Sources & evidence

ORD record
ord-0fb65beb2d9940c0831f67a636f6215b
Source dataset
uspto-grants-2013_04
Patent number
US08410119B2

Reaction notes

Loading…