Triethylamine → HCID 21897708, compound

HRID 1864101Notes

Reaction equation

HRID 1864101 reaction equation
N1([C:6](N2C=CN=C2)=[O:7])C=CN=C1.[CH:13]1([CH2:17][OH:18])[CH2:16][CH2:15][CH2:14]1.Cl.[F:20][C:21]1[CH:26]=[C:25]([S:27]([CH3:30])(=[O:29])=[O:28])[CH:24]=[CH:23][C:22]=1[N:31]1[C:35]2=[N:36][CH:37]=[N:38][C:39]([S:40][CH:41]3[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]3)=[C:34]2[CH:33]=[N:32]1.C(N(CC)CC)C>CS(C)=O>[CH:13]1([CH2:17][O:18][C:6]([N:44]2[CH2:43][CH2:42][CH:41]([S:40][C:39]3[N:38]=[CH:37][N:36]=[C:35]4[N:31]([C:22]5[CH:23]=[CH:24][C:25]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:26][C:21]=5[F:20])[N:32]=[CH:33][C:34]=34)[CH2:46][CH2:45]2)=[O:7])[CH2:16][CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 78130CyclobutylcarbinolHCID 21897830HCID 21897830, compound

Product 1

HCID 21897708HCID 21897708, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Di-imidazol-1-yl-methanone (0.25 mmol, 41 mg), and cyclobutyl methanol (0.25 mmol, 24 μL) were dissolved in DMSO (2 mL) and stirred for 30 minutes at room temperature. Then, 1-(2-fluoro-4-methanesulfonyl-phenyl)-4-(piperidin-4-ylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidine hydrochloride (0.18 mmol, 80 mg) and triethylamine (0.54 mmol, 75 μL) were added. The mixture was heated in a microwave for 5 minutes at 120° C. The progress of the reaction was monitored by thin layer chromatography and LCMS. Purification by HPLC provided Compound A113 as a white solid (29 mg, 31%). 1H NMR (400 MHz, CDCl3) δ (ppm): 8.71 (s, 1H); 8.22 (s, 1H); 7.87 (m, 3H); 4.37 (h, 1H); 4.00 (m, 4H); 3.16 (m, 2H); 3.05 (s, 3H); 2.56 (m, 1H); 2.12 (m, 2H); 2.01 (m, 2H); 1.85 (m, 2H); 1.73 (m, 4H). Exact mass calculated for C23H26FN5O4S2 519.61, found 520.3 (MH+).

Workup

  1. temperatureThe mixture was heated in a microwave for 5 minutes at 120° C
  2. customPurification by HPLC

Sources & evidence

ORD record
ord-86e76b53c8ba42eb9080cf25a1bc3e7e
Source dataset
uspto-grants-2009_12
Patent number
US07625906B2

Reaction notes

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