Water → HCID 22249558, compound

HRID 890210Notes

Reaction equation

HRID 890210 reaction equation
C(N(CC)CC)C.[C:8]1([CH3:30])[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH3:15])[C:9]=1[C:16]1[C:17]([CH3:29])=[N:18][N:19]2[C:24]3[NH:25][CH2:26][CH2:27][C:23]=3[C:22]([CH3:28])=[N:21][C:20]=12.[CH2:31]([S:35](Cl)(=[O:37])=[O:36])[CH2:32][CH2:33][CH3:34].O>ClCCl>[CH2:31]([S:35]([N:25]1[C:24]2[N:19]3[N:18]=[C:17]([CH3:29])[C:16]([C:9]4[C:8]([CH3:30])=[CH:13][C:12]([CH3:14])=[CH:11][C:10]=4[CH3:15])=[C:20]3[N:21]=[C:22]([CH3:28])[C:23]=2[CH2:27][CH2:26]1)(=[O:37])=[O:36])[CH2:32][CH2:33][CH3:34]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 754301-Butanesulfonyl chlorideHCID 135593031HCID 135593031, compound

Product 1

HCID 22249558HCID 22249558, compoundYield 27.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (0.091 mL, 0.652 mmol) was added to a solution of 3-mesityl-2,5-dimethyl-7,8-dihydro-6H-pyrazolo[1,5-a]pyrrolo[3,2-e]pyrimidine (100 mg, 0.326 mmol) prepared in Example 72 in dichloromethane (5 mL). Butanesulfonyl chloride (0.047 mL, 0.358 mmol) was added dropwise at room temperature, followed by stirring for two hours. Water was added to the reaction solution, extracted with ethyl acetate, washed with brine, dried over MgSO4, and the solvent was evaporated. The residue was subjected to silica gel column cromatography, to give the title compound (38 mg, 27%) as white crystals from a fraction of ethyl acetate-hexane (1:4 v/v).

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-26eab54167304046b7e42f6c0b317800
Source dataset
uspto-grants-2006_02
Patent number
US06995163B2

Reaction notes

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