Triethylamine → HCID 21897598, compound

HRID 1864100Notes

Reaction equation

HRID 1864100 reaction equation
N1([C:6](N2C=CN=C2)=[O:7])C=CN=C1.[CH:13]1([CH2:16][OH:17])[CH2:15][CH2:14]1.Cl.[F:19][C:20]1[CH:25]=[C:24]([S:26]([CH3:29])(=[O:28])=[O:27])[CH:23]=[CH:22][C:21]=1[N:30]1[C:34]2=[N:35][CH:36]=[N:37][C:38]([S:39][CH:40]3[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]3)=[C:33]2[CH:32]=[N:31]1.C(N(CC)CC)C>CS(C)=O>[CH:13]1([CH2:16][O:17][C:6]([N:43]2[CH2:42][CH2:41][CH:40]([S:39][C:38]3[N:37]=[CH:36][N:35]=[C:34]4[N:30]([C:21]5[CH:22]=[CH:23][C:24]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:25][C:20]=5[F:19])[N:31]=[CH:32][C:33]=34)[CH2:45][CH2:44]2)=[O:7])[CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 75644CyclopropanemethanolHCID 21897830HCID 21897830, compound

Product 1

HCID 21897598HCID 21897598, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Di-imidazol-1-yl-methanone (0.25 mmol, 41 mg), and cyclopropylmethanol (0.25 mmol, 20 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 RPLC provided Compound A112 as a white solid (26 mg, 29%). 1H NMR (400 MHz, CDCl3) δ (ppm): 8.72 (s, 1H); 8.41 (s, 1H); 7.87 (m, 3H); 4.40 (h, 1H); 4.01 (m, 2H); 3.87 (d, 2H); 3.19 (m, 2H); 3.06 (s, 3H); 2.17 (m, 2H); 1.73 (m, 2H); 1.07 (m, 1H); 0.51 (m, 2H); 0.25 (m, 2H). Exact mass calculated for C22H24FN5O4S2 505.59, found 506.20 (MH+).

Workup

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

Sources & evidence

ORD record
ord-c6e96ad58433421e887f6a1891b0449c
Source dataset
uspto-grants-2009_12
Patent number
US07625906B2

Reaction notes

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