Triethylamine → N-[4-[(6,7-Dihydro-2-methyl-5H-pyrimido[5,4-d] [1]-benzazepin-7-yl)carbonyl]phenyl]-2-methylbenzamide

HRID 355934Notes

Reaction equation

HRID 355934 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][C:5]2[CH2:6][CH2:7][N:8]([C:17](=[O:25])[C:18]3[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][CH:19]=3)[C:9]3[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=3[C:11]=2[N:12]=1.C(N(CC)CC)C.[CH3:33][C:34]1[CH:42]=[CH:41][CH:40]=[CH:39][C:35]=1[C:36](Cl)=[O:37]>C(Cl)Cl>[CH3:1][C:2]1[N:3]=[CH:4][C:5]2[CH2:6][CH2:7][N:8]([C:17]([C:18]3[CH:19]=[CH:20][C:21]([NH:24][C:36](=[O:37])[C:35]4[CH:39]=[CH:40][CH:41]=[CH:42][C:34]=4[CH3:33])=[CH:22][CH:23]=3)=[O:25])[C:9]3[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=3[C:11]=2[N:12]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 702762-Methylbenzoyl chlorideHCID 571051316,7-Dihydro-2-methyl-7-(4-aminobenzoyl)-5H-pyrimido-[5,4-d][1]benzazepine

Product 1

HCID 15307997N-[4-[(6,7-Dihydro-2-methyl-5H-pyrimido[5,4-d] [1]-benzazepin-7-yl)carbonyl]phenyl]-2-methylbenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 0.216 mg of 6,7-dihydro-2-methyl-7-(4-aminobenzoyl)-5H-pyrimido[5,4-d][1]benzazepine in 6 ml of methylene chloride under argon is added 100 μl of triethylamine followed by a solution of 94 μl of 2-methylbenzoyl chloride in 1.5 ml of methylene chloride. The reaction mixture is stirred at room temperature for 18 hours, washed with water, saturated 5 NaHCO3 and the separated organic layer treated with activated carbon and filtered through MgSO4. The filtrate is evaporated to a residue which is dissolved in ethyl acetate and evaporated in vacuo to give 300 mg of the desired product as a pale yellow foam. HR FABMS: Exact Mass (M+H):449.1974.

Workup

  1. washwashed with water, saturated 5 NaHCO3
  2. additionthe separated organic layer treated with activated carbon
  3. filtrationfiltered through MgSO4
  4. customThe filtrate is evaporated to a residue which
  5. dissolutionis dissolved in ethyl acetate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-843e899d032a4022a43230ff57323c1b
Source dataset
uspto-grants-1998_11
Patent number
US05834461

Reaction notes

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