Cyclohexanone → HCID 178522144, compound

HRID 20289Notes

Reaction equation

HRID 20289 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[C:15]([NH2:16])=[CH:14][NH:13][N:12]=2)=[O:10])=[CH:4][CH:3]=1.[C:17]1(=O)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[C:15]([NH:16][CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)=[CH:14][NH:13][N:12]=2)=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7967CyclohexanoneHCID 5049666Sodium triacetoxyborohydrideHCID 178508056HCID 178508056, compound

Product 1

HCID 178522144HCID 178522144, compoundYield 15.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-amino-1H-pyrazole-3-carboxylic acid (4-fluoro-phenyl)-amide (200 mg; 1 mmol) and cyclohexanone (107 mg; 1.1 mmol) in dichloromethane (10 ml) were added 3 Å molecular sieves (1 g) and sodium triacetoxyborohydride (315 mg; 1.5 mmol), and the mixture was then stirred at room temperature over the weekend. The reaction mixture was filtered through Celite®, diluted with ethyl acetate, washed with brine, dried (MgSO4) and evaporated to give the 48 mg of the product as a grey gum. (LC/MS: Rt 2.95, [M+H]+ 285).

Workup

  1. filtrationThe reaction mixture was filtered through Celite®
  2. additiondiluted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-dcb2307e136e4b1189f2da3b32c6ceb2
Source dataset
uspto-grants-2010_06
Patent number
US07745638B2

Reaction notes

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