HCID 57486807, compound → HCID 58689748, compound

HRID 1911736Notes

Reaction equation

HRID 1911736 reaction equation
[F:1][C:2]([F:40])([F:39])[C:3]1[CH:4]=[C:5]([CH:32]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:34]=1)[CH2:6][N:7]([CH2:11][C:12]1[CH:13]=[C:14]2[C:29]([CH3:30])=[N:28][N:27]([CH3:31])[C:15]2=[N:16][C:17]=1[N:18]([CH2:21][CH:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1)[CH2:19][CH3:20])[C:8]([NH2:10])=[O:9]>C(O)(C)(C)C>[F:40][C:2]([F:39])([F:1])[C:3]1[CH:4]=[C:5]([CH:32]=[C:33]([C:35]([F:37])([F:38])[F:36])[CH:34]=1)[CH2:6][N:7]([CH2:11][C:12]1[CH:13]=[C:14]2[C:29]([CH3:30])=[N:28][N:27]([CH3:31])[C:15]2=[N:16][C:17]=1[N:18]([CH2:21][CH:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1)[CH2:19][CH3:20])[C:8]1[O:9][CH:34]=[C:3]([C:2]([F:40])([F:39])[F:1])[N:10]=1

Participants

3

Reactant 1

HCID 57486807HCID 57486807, compound

Product 1

HCID 58689748HCID 58689748, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To a stirred solution of 1-(3,5-bis-trifluoromethyl-benzyl)-1-[6-(cyclopentylmethyl-ethyl-amino)-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-ylmethyl]-urea (0.250 g, 0.430 mmol) in tert-butanol (10 mL) was added 1,1,1-trifluoromethyl acetyl bromide (0.20 g, 0.480 mmol). This mixture was refluxed for 3 h and then cooled to RT. After concentration in vacuo, water (10 mL) was added to the residue, and the product was extracted with ethyl acetate (3×25 mL). The combined organic layers were dried over sodium sulfate and concentrated under vacuum to afford the crude residue, which was purified by column chromatography over 100-200 mesh silica gel using 5% ethyl acetate and petroleum ether, to yield the title compound as a white solid (yield: 20%).

Workup

  1. temperatureThis mixture was refluxed for 3 h
  2. concentrationAfter concentration in vacuo, water (10 mL)
  3. additionwas added to the residue
  4. extractionthe product was extracted with ethyl acetate (3×25 mL)
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customto afford the crude residue, which
  8. customwas purified by column chromatography over 100-200 mesh silica gel using 5% ethyl acetate and petroleum ether

Sources & evidence

ORD record
ord-dd737ebada484b3899b7f7a31fa38eb0
Source dataset
uspto-grants-2013_12
Patent number
US08604055B2

Reaction notes

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