HCID 86626334, compound → HCID 67202647, compound

HRID 1921096Notes

Reaction equation

HRID 1921096 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]2[CH2:17][CH2:16][C:15]3[N:18]([C:28]([C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=4)([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[N:19]=[C:20]([NH:21]C(=O)C(F)(F)F)[C:14]=3[CH2:13]2)(=[O:11])=[O:10])[CH:5]=[C:6]([F:8])[CH:7]=1>CO.C(N(CC)CC)C>[F:8][C:6]1[CH:5]=[C:4]([S:9]([N:12]2[CH2:17][CH2:16][C:15]3[N:18]([C:28]([C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=4)([C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=4)[C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[N:19]=[C:20]([NH2:21])[C:14]=3[CH2:13]2)(=[O:11])=[O:10])[CH:3]=[C:2]([F:1])[CH:7]=1

Participants

4

Reactant 1

HCID 86626334HCID 86626334, compound

Product 1

HCID 67202647HCID 67202647, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8471TriethylamineSolvent

Procedure

To a suspension of N-[5-(3,5-difluoro-benzenesulfonyl)-1-trityl-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridin-3-yl]-2,2,2-trifluoro-acetamide (106.65 mmol) in methanol (500 mL), triethylamine (150 mL) was added and the mixture was refluxed for 36 hours and then evaporated to dryness. The crude was treated with a mixture of diethylether (400 mL) and methanol (100 mL), stiffed at room temperature for 30 min., filtered and washed with diethylether. After drying in vacuo the title compound was obtained as white solid (50.5 g, 86%).

Workup

  1. additionwas added
  2. temperaturethe mixture was refluxed for 36 hours
  3. customevaporated to dryness
  4. additionThe crude was treated with a mixture of diethylether (400 mL) and methanol (100 mL)
  5. filtrationfiltered
  6. washwashed with diethylether
  7. dry with materialAfter drying in vacuo the title compound

Sources & evidence

ORD record
ord-0e6e289c71d248c7b96152239b61bf37
Source dataset
uspto-grants-2012_05
Patent number
US08173659B2

Reaction notes

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