Triethylamine → Methyl 4-{{4-[2-(1-ethyl-6,11-dihydro-5-methyl-6-oxo-5h-dipyrido[3,2-b:2',3'-e][1,4]diazepin-8-yl)ethoxy]-3-methylbenzoyl}amino}benzoate

HRID 393294Notes

Reaction equation

HRID 393294 reaction equation
C([N:3]1[C:9]2[N:10]=[CH:11][C:12]([CH2:14][CH2:15][O:16][C:17]3[CH:25]=[CH:24][C:20]([C:21](Cl)=[O:22])=[CH:19][C:18]=3[CH3:26])=[CH:13][C:8]=2[C:7](=[O:27])[N:6]([CH3:28])[C:5]2[CH:29]=[CH:30][CH:31]=[N:32][C:4]1=2)C.[NH2:33][C:34]1[CH:43]=[CH:42][C:37]([C:38]([O:40][CH3:41])=[O:39])=[CH:36][CH:35]=1.[CH3:44][CH2:45]N(CC)CC>C(Cl)Cl.CCOC(C)=O>[CH2:44]([N:32]1[C:4]2[NH:3][C:9]3[N:10]=[CH:11][C:12]([CH2:14][CH2:15][O:16][C:17]4[CH:25]=[CH:24][C:20]([C:21]([NH:33][C:34]5[CH:35]=[CH:36][C:37]([C:38]([O:40][CH3:41])=[O:39])=[CH:42][CH:43]=5)=[O:22])=[CH:19][C:18]=4[CH3:26])=[CH:13][C:8]=3[C:7](=[O:27])[N:6]([CH3:28])[C:5]=2[CH:29]=[CH:30][CH2:31]1)[CH3:45]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 12082Methyl 4-aminobenzoateHCID 226488664-[2-(11-Ethyl-6,11-dihydro-5-methyl-6-oxo-5h-dipyrido[3,2-b:2',3'-e][1,4]diazepin-8-yl)ethoxy]-3-methyl benzoyl chloride

Product 1

HCID 22648879Methyl 4-{{4-[2-(1-ethyl-6,11-dihydro-5-methyl-6-oxo-5h-dipyrido[3,2-b:2',3'-e][1,4]diazepin-8-yl)ethoxy]-3-methylbenzoyl}amino}benzoateYield 76%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-[2-(11-ethyl-6,11-dihydro-5-methyl-6-oxo-5H-dipyrido[3,2-b:2′,3′-e][1,4]diazepin-8-yl)ethoxy]-3-methylbenzoyl chloride (47.0 mg, 0.11 mmol), methyl 4-aminobenzoate (15.8 mg, 0.11 mmol) and Et3N (15.3 μL, 0.11 mmol) in CH2Cl2 (4 mL) was stirred at 25° C. for 5 h. The reaction mixture was diluted with EtOAc and the resulting solution was successively washed with aqueous saturated NaHCO3 solution and brine, dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (Hexane:EtOAc, 1:1) to give the title compound (45 mg, 76% yield) as a white solid.

Workup

  1. washthe resulting solution was successively washed with aqueous saturated NaHCO3 solution and brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography (Hexane:EtOAc, 1:1)

Sources & evidence

ORD record
ord-ba01f49ec2594debaa1a45705993fdce
Source dataset
uspto-grants-2004_10
Patent number
US06806265B2

Reaction notes

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