HCID 67497844, compound → HCID 67498800, compound

HRID 1919556Notes

Reaction equation

HRID 1919556 reaction equation
[C:1]1([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH:6]=[CH:5][C:4]([N:7]2[CH:16]([CH2:17][C:18]([O:20][CH3:21])=[O:19])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]=[C:8]2[N:22]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][N:29](CC2C=CC=CC=2)CC2C=CC=CC=2)[CH3:23])=[CH:3][CH:2]=1>CO>[NH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][N:22]([C:8]1[N:7]([C:4]2[CH:3]=[CH:2][C:1]([C:44]3[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=3)=[CH:6][CH:5]=2)[CH:16]([CH2:17][C:18]([O:20][CH3:21])=[O:19])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1)[CH3:23]

Participants

3

Reactant 1

HCID 67497844HCID 67497844, compound

Product 1

HCID 67498800HCID 67498800, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-(4-biphenylyl)-2-[N-(5-dibenzylaminopentyl)-N-methylamino]-4-methoxycarbonylmethyl-3,4-dihydroquinazoline (19) (362 mg, 0.556 mmol) in methanol (20 ml) was added 10% Pd(C) (883 mg), and the reaction mixture was stirred under hydrogen atmosphere for 24 hours. After the reaction was completed, the resulting reaction mixture was filtered with celite, extracted with dichloromethane three times and washed with a saline solution. The combined organic phase was dried with anhydrous magnesium sulfate and distilled under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluent: dichloromethane:methanol:ammonia water=100:9:1) to give the target compound as a yellow liquid (110 mg, 42%).

Workup

  1. customthe resulting reaction mixture
  2. filtrationwas filtered with celite
  3. extractionextracted with dichloromethane three times
  4. washwashed with a saline solution
  5. dry with materialThe combined organic phase was dried with anhydrous magnesium sulfate
  6. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-bfa10d851d6e4a67ad8fcae185565ae0
Source dataset
uspto-grants-2012_05
Patent number
US08168646B2

Reaction notes

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