Cyclohexanecarboxaldehyde → HCID 22558437, compound

HRID 984441Notes

Reaction equation

HRID 984441 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:14][C:15](=[O:29])[C:16]([NH:18][C:19]([CH3:28])([CH3:27])[CH2:20][N:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)=[O:17])[CH:6]=[CH:7][C:8]=1[C:9]1[O:13][CH:12]=[N:11][CH:10]=1.[CH:30]1([CH:36]=O)[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1.C(O)(=O)C.ClCCl.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH:30]1([CH2:36][N:24]2[CH2:23][CH2:22][N:21]([CH2:20][C:19]([NH:18][C:16](=[O:17])[C:15]([NH:14][C:5]3[CH:6]=[CH:7][C:8]([C:9]4[O:13][CH:12]=[N:11][CH:10]=4)=[C:3]([O:2][CH3:1])[CH:4]=3)=[O:29])([CH3:27])[CH3:28])[CH2:26][CH2:25]2)[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1

Participants

6

Reactant 4

HCID 16275CyclohexanecarboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 21922555Acetic acid methylene chloride2×HCID 22558368HCID 22558368, compound

Product 1

HCID 22558437HCID 22558437, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 48 mg of N-[3-methoxy-4-(5-oxazolyl)phenyl]-N′-[1,1-dimethyl-2-(1-piperazinyl)ethyl]oxalamide (1.2 mmol) and 13 mg of cyclohexanecarboxaldehyde (1.2 mmol) in 1 ml of a 5% acetic acid/dichloromethane mixture was treated with a solution of 38 mg of sodium triacetoxyborohydride (1.8 mmol) in 1 ml of a 5% acetic acid/dichloromethane mixture. After stirring overnight at room temperature the reaction mixture was diluted with 10 ml of dichloromethane and washed with 8 ml of a sodium bicarbonate solution followed by 8 ml of water. The organic layer was then evaporated and purified using flash chromatography on a silica gel column eluting with 5% methanol/dichloromethane to give after evaporation of the fractions 14.3 mg (0.3 mmol, 25%) of N-[2-[4-(cyclohexylmethyl)-1-piperazinyl-1,1-dimethylethyl]-N′-[3-methoxy-4-(5-oxazolyl)phenyl]oxalamide in the form of a white solid. MS: m/e 498.2 [M+H]+.

Workup

  1. washwashed with 8 ml of a sodium bicarbonate solution
  2. customThe organic layer was then evaporated
  3. custompurified
  4. washeluting with 5% methanol/dichloromethane
  5. customto give
  6. customafter evaporation of the fractions 14.3 mg (0.3 mmol, 25%) of N-[2-[4-(cyclohexylmethyl)-1-piperazinyl-1,1-dimethylethyl]-N′-[3-methoxy-4-(5-oxazolyl)phenyl]oxalamide in the form of a white solid

Sources & evidence

ORD record
ord-58b5b70373ff484fa17127d5319457a0
Source dataset
uspto-grants-2005_03
Patent number
US06867299B2

Reaction notes

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