Benzoyl chloride → HCID 10140073, compound

HRID 984433Notes

Reaction equation

HRID 984433 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.[NH2:17][CH2:18][C:19]1[CH:20]=[C:21]([NH:25][C:26](=[O:43])[C:27]([NH:29][C:30]2[CH:35]=[CH:34][C:33]([C:36]3[O:40][CH:39]=[N:38][CH:37]=3)=[C:32]([O:41][CH3:42])[CH:31]=2)=[O:28])[CH:22]=[CH:23][CH:24]=1.C(N(CC)CC)C>CN(C)C=O.ClCCl>[C:1]([NH:17][CH2:18][C:19]1[CH:20]=[C:21]([NH:25][C:26](=[O:43])[C:27]([NH:29][C:30]2[CH:35]=[CH:34][C:33]([C:36]3[O:40][CH:39]=[N:38][CH:37]=3)=[C:32]([O:41][CH3:42])[CH:31]=2)=[O:28])[CH:22]=[CH:23][CH:24]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 22558403HCID 22558403, compound

Product 1

HCID 10140073HCID 10140073, compoundYield 45.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

29 mg (0.21 mmol) of benzoyl chloride were added to a solution of 100 mg (0.21 mmol) of N-[3-(aminomethyl)phenyl]-N′-[3-methoxy-4-(5-oxazolyl)phenyl]oxalamide trifluoroacetate, prepared as described in Example 3 above, and 46 mg (0.46 mmol) of triethylamine in a mixture of 2 ml of dimethylformamide and 5 ml of dichloromethane, and stirred at room temperature for 18 hours. The solution was washed with 2M hydrochloric acid and saturated sodium bicarbonate then dried over magnesium sulphate and evaporated to dryness. The residue was chromatographed on silica gel using ethyl acetate/petrol (2:1) for the elution. After trituration with diethyl ether there was obtained 45 mg of N-[3-(benzamidomethyl)phenyl]-N′-[3-methoxy-4-(5-oxazolyl)phenyl]oxalamide as a white solid. MS: m/e 471.0 [M+H]+.

Workup

  1. customprepared
  2. washThe solution was washed with 2M hydrochloric acid and saturated sodium bicarbonate
  3. dry with materialthen dried over magnesium sulphate
  4. customevaporated to dryness
  5. customThe residue was chromatographed on silica gel
  6. washfor the elution

Sources & evidence

ORD record
ord-9ce286b4b18a4af687611fb6a9ff5b15
Source dataset
uspto-grants-2005_03
Patent number
US06867299B2

Reaction notes

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