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

HRID 2293282Notes

Reaction equation

HRID 2293282 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 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 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-e03e8ac5b5624bc18d6a6305cfd78cdd
Source dataset
uspto-grants-1997_11
Patent number
US05686445

Reaction notes

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