N,N-Dimethylglycine → 2-Dimethylamino-N-(5,5-dimethyl-8-nitro-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl)-acetamide

HRID 1687655Notes

Reaction equation

HRID 1687655 reaction equation
[CH3:1][N:2]([CH2:4][C:5]([OH:7])=O)[CH3:3].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.CN(C=O)C.[NH2:35][CH:36]1[CH2:42][C:41]([CH3:44])([CH3:43])[C:40]2[CH:45]=[CH:46][C:47]([N+:49]([O-:51])=[O:50])=[CH:48][C:39]=2[NH:38][C:37]1=[O:52]>CCOCC>[CH3:1][N:2]([CH3:3])[CH2:4][C:5]([NH:35][CH:36]1[CH2:42][C:41]([CH3:44])([CH3:43])[C:40]2[CH:45]=[CH:46][C:47]([N+:49]([O-:51])=[O:50])=[CH:48][C:39]=2[NH:38][C:37]1=[O:52])=[O:7]

Participants

7

Reactant 5

HCID 673N,N-DimethylglycineHCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 672640283-amino-5,5-dimethyl-8-nitro-3,4-dihydro-1H-1-benzazepin-2-one

Product 1

HCID 672640872-Dimethylamino-N-(5,5-dimethyl-8-nitro-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl)-acetamide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Dimethylamino-acetic acid (0.124 g, 1.20 mmol), EDCl (0.461 g, 2.41 mmol), HOBT (0.276 g, 2.05 mmol) and DMF (1.00 mL, 12.9 mmol) were stirred at rt for 30 minutes, followed by the addition of TEA (0.235 mL, 1.68 mmol) and 3-Amino-5,5-dimethyl-8-nitro-1,3,4,5-tetrahydro-1-benzazepin-2-one (0.300 g, 1.20 mmol). The reaction mixture was stirred at rt for 3 h, diluted with ether and washed with water. The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure. Title compound was isolated as a white solid (80 mg, 20%).

Workup

  1. washwashed with water
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b545b81411d948b3b3c876b56e456cfd
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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