Triethylamine → N-[4-[(4,5-Dihydro-2-methylpyrazolo[4,3-d] [1]benzazepin-6(2H)-yl)carbonyl]phenyl]-2-methylbenzamide

HRID 1957676Notes

Reaction equation

HRID 1957676 reaction equation
[CH3:1][N:2]1[CH:24]=[C:5]2[CH2:6][CH2:7][N:8]([C:15](=[O:23])[C:16]3[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=3)[C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:4]2=[N:3]1.C(N(CC)CC)C.[CH3:32][C:33]1[CH:41]=[CH:40][CH:39]=[CH:38][C:34]=1[C:35](Cl)=[O:36]>C(Cl)Cl.O1CCOCC1>[CH3:1][N:2]1[CH:24]=[C:5]2[CH2:6][CH2:7][N:8]([C:15]([C:16]3[CH:17]=[CH:18][C:19]([NH:22][C:35](=[O:36])[C:34]4[CH:38]=[CH:39][CH:40]=[CH:41][C:33]=4[CH3:32])=[CH:20][CH:21]=3)=[O:23])[C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:4]2=[N:3]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 702762-Methylbenzoyl chlorideHCID 538901292,4,5,6-Tetrahydro-2-methyl-6-(4-aminobenzoyl)-pyrazolo[4,3-d][1]benzazepine

Product 1

HCID 9932748N-[4-[(4,5-Dihydro-2-methylpyrazolo[4,3-d] [1]benzazepin-6(2H)-yl)carbonyl]phenyl]-2-methylbenzamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a mixture of 0.420 g of 2,4,5,6-tetrahydro-2-methyl-6-(4-aminobenzoyl)pyrazolo[4,3-d][1]-benzazepine and 275 p1 of triethylamine in 6 ml of methylene chloride and 2 ml of dioxane is added a solution of 215 p1 of 2-methylbenzoyl chloride in 1.5 ml of dioxane. The reactants are stirred under argon for 4.5 hours. The volatiles are evaporated in vacuo to a residue which is dissolved in methylene chloride and washed with 10% NaHCO3 and brine. The organic layer is treated with activated carbon, dried with MgSO4 and evaporated in vacuo to give 660 mg of a tan foam residue. The residue is purified by column chromatography on silica gel by elution with 30% ethyl acetate-methylene chloride to give 590 mg of the desired product as white crystalline solid, m.p. 246°-248° C; HR FABMS: (M+H)=437.1972.

Workup

  1. customThe volatiles are evaporated in vacuo to a residue which
  2. dissolutionis dissolved in methylene chloride
  3. washwashed with 10% NaHCO3 and brine
  4. additionThe organic layer is treated with activated carbon
  5. dry with materialdried with MgSO4
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-4aaa2aeb83fd49cebc4ba60e1450fd37
Source dataset
uspto-grants-1998_07
Patent number
US05786353

Reaction notes

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