Diisopropylethylamine → HCID 53257253, compound

HRID 1931774Notes

Reaction equation

HRID 1931774 reaction equation
[CH2:1]([S:5](Cl)(=[O:7])=[O:6])[CH:2]([CH3:4])[CH3:3].FC(F)(F)C(O)=O.[CH3:16][S:17]([C:20]1[CH:41]=[CH:40][C:23]([O:24][C:25]2[N:30]=[CH:29][N:28]=[C:27]3[N:31]([CH:34]4[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]4)[N:32]=[CH:33][C:26]=23)=[CH:22][CH:21]=1)(=[O:19])=[O:18].C(N(C(C)C)CC)(C)C>ClCCl>[CH3:16][S:17]([C:20]1[CH:21]=[CH:22][C:23]([O:24][C:25]2[N:30]=[CH:29][N:28]=[C:27]3[N:31]([CH:34]4[CH2:35][CH2:36][N:37]([S:5]([CH2:1][CH:2]([CH3:4])[CH3:3])(=[O:7])=[O:6])[CH2:38][CH2:39]4)[N:32]=[CH:33][C:26]=23)=[CH:40][CH:41]=1)(=[O:19])=[O:18]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1822361-Propanesulfonyl chloride, 2-methyl-HCID 669153264-(4-methanesulfonyl-phenoxy)-1-piperidin-4-yl-1H-pyrazolo[3,4-d]pyrimidine trifluoroacetate salt2×

Product 1

HCID 53257253HCID 53257253, compoundYield 43.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Isobutanesulfonyl chloride (Aldrich Chemical Company, Inc., Milwaukee, Wis., USA; 23 mg, 0.15 mmol) was added dropwise to a stirred solution of 4-(4-methanesulfonyl-phenoxy)-1-piperidin-4-yl-1H-pyrazolo[3,4-d]pyrimidine trifluoroacetate salt (Intermediate 27; 60 mg, 0.12 mmol) and diisopropylethylamine (0.11 mL, 0.62 mmol) in dichloromethane (1 mL) at room temperature. The mixture was stirred at room temperature for 1 h and then washed with water. The organic layers was dried (sodium sulfate), filtered, evaporated, triturated with ether and purified by HPLC to give to give 4-(4-methanesulfonyl-phenoxy)-1-[1-(2-methyl-propane-1-sulfonyl)-piperidin-4-yl]-1H-pyrazolo[3,4-d]pyrimidine (26 mg, 43%) as a white solid.

Workup

  1. washwashed with water
  2. dry with materialThe organic layers was dried (sodium sulfate)
  3. filtrationfiltered
  4. customevaporated
  5. customtriturated with ether
  6. custompurified by HPLC
  7. customto give

Sources & evidence

ORD record
ord-69ff0e348bfb48788800c5eac0fc25e4
Source dataset
uspto-grants-2012_05
Patent number
US08188098B2

Reaction notes

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