4-Methylbenzaldehyde → HCID 22558382, compound

HRID 984435Notes

Reaction equation

HRID 984435 reaction equation
[NH2:1][CH2:2][C:3]([NH:6][C:7](=[O:24])[C:8]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[O:21][CH:20]=[N:19][CH:18]=2)=[C:13]([O:22][CH3:23])[CH:12]=1)=[O:9])([CH3:5])[CH3:4].[CH3:25][C:26]1[CH:33]=[CH:32][C:29]([CH:30]=O)=[CH:28][CH:27]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.C(O)(=O)C.ClCCl>[CH3:23][O:22][C:13]1[CH:12]=[C:11]([NH:10][C:8](=[O:9])[C:7]([NH:6][C:3]([CH3:5])([CH3:4])[CH2:2][NH:1][CH2:25][C:26]2[CH:33]=[CH:32][C:29]([CH3:30])=[CH:28][CH:27]=2)=[O:24])[CH:16]=[CH:15][C:14]=1[C:17]1[O:21][CH:20]=[N:19][CH:18]=1

Participants

6

Reactant 3

HCID 77254-MethylbenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 22558401HCID 22558401, compound

Product 1

HCID 22558382HCID 22558382, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21922555Acetic acid methylene chlorideSolvent

Procedure

30 mg (0.09 mmol) of N-(2-amino-1,1-dimethyl-ethyl)-N′-(3-methoxy-4-oxazol-5-yl-phenyl)-oxalamide, 11.3 mg (0.095 mmol) of 4-methylbenzaldehyde and 30 mg (0.14 mmol) of sodium triacetoxyborohydride were dissolved in 2 ml of a 5% acetic acid dichloromethane mixture for 16 hours. The reaction mixture was then diluted with 8 ml of dichloromethane and washed with water, saturated sodium hydrogen carbonate and brine. The resulting organic solution was then dried with magnesium sulphate, filtered and evaporated to give N-[3-methoxy-4-(5-oxazolyl)phenyl-N′-[2-(4-methylbenzylamino)-1,1-dimethylethyl]oxalamide as a yellow solid MS: m/e 437.3 [M+H]+.

Workup

  1. washwashed with water, saturated sodium hydrogen carbonate and brine
  2. dry with materialThe resulting organic solution was then dried with magnesium sulphate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-1b7b7f10513d4d708f209d9bd453fef3
Source dataset
uspto-grants-2005_03
Patent number
US06867299B2

Reaction notes

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