Dimethylformamide → 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-methyl benzoyl chloride

HRID 393293Notes

Reaction equation

HRID 393293 reaction equation
[C:1]([Cl:6])([C:3](Cl)=O)=[O:2].CN(C=O)C.[CH2:12]([N:14]1[C:20]2[N:21]=[CH:22][C:23]([CH2:25][CH2:26][O:27][C:28]3[CH:36]=[CH:35]C(C(O)=O)=[CH:30][C:29]=3[CH3:37])=[CH:24][C:19]=2[C:18](=[O:38])[N:17]([CH3:39])[C:16]2[CH:40]=[CH:41][CH:42]=[N:43][C:15]1=2)[CH3:13]>C(Cl)Cl>[CH2:12]([N:14]1[C:20]2[N:21]=[CH:22][C:23]([CH2:25][CH2:26][O:27][C:28]3[CH:36]=[CH:35][C:3]([C:1]([Cl:6])=[O:2])=[CH:30][C:29]=3[CH3:37])=[CH:24][C:19]=2[C:18](=[O:38])[N:17]([CH3:39])[C:16]2[CH:40]=[CH:41][CH:42]=[N:43][C:15]1=2)[CH3:13]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 30120204-[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-methylbenzoic acid

Product 1

HCID 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 chlorideYield 101.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(COCl)2 (25 μL, 0.87 mmol) and DMF (10 μL) were added to 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-methylbenzoic acid (52.8 mg, 0.12 mmol) in CH2Cl2 (5 mL). The reaction mixture was heated to reflux for 1 h. The cooled mixture was concentrated under reduced pressure to give the title compound (55 mg, 100% yield), which was used without further purification.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 1 h
  3. concentrationThe cooled mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-dd7f7bb895e4423d992cd486a6b17c05
Source dataset
uspto-grants-2004_10
Patent number
US06806265B2

Reaction notes

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