Dimethylamine, hydrochloride → 10-bromo-N3,N3-dimethyl-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2,3-dicarboxamide

HRID 575313

Reaction equation

HRID 575313 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:11]3[CH2:12][CH:9]([CH2:10]3)[N:8]3[C:13]([C:19](O)=[O:20])=[C:14]([C:16](=[O:18])[NH2:17])[N:15]=[C:7]3[C:6]=2[CH:22]=1.Cl.[CH3:24][NH:25][CH3:26]>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:11]3[CH2:10][CH:9]([CH2:12]3)[N:8]3[C:13]([C:19]([N:25]([CH3:26])[CH3:24])=[O:20])=[C:14]([C:16]([NH2:17])=[O:18])[N:15]=[C:7]3[C:6]=2[CH:22]=1

Participants

3

Reactant 2

HCID 10473Dimethylamine, hydrochlorideHCID 8669334810-bromo-2-carbamoyl-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-3-carboxylic acid

Product 1

HCID 8669334710-bromo-N3,N3-dimethyl-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2,3-dicarboxamide

Procedure

10-bromo-2-carbamoyl-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-3-carboxylic acid (0.1 g) was reacted with N,N-Dimethylamine Hydrochloride similarly to the conditions described in Example 2 to produce 10-bromo-N3,N3-dimethyl-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2,3-dicarboxamide. This intermediate was then reacted with (2R)-2-(5-methylisoxazol-3-yl)but-3-yn-2-ol via General Procedure E to afford 21 mg (16%) of 10-[(3R)-3-hydroxy-3-(5-methylisoxazol-3-yl)but-1-ynyl]-N3,N3-dimethyl-5,6,7,12-tetrahydro-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2,3-dicarboxamide.

Sources & evidence

ORD record
ord-5371f8b95f16449fa49a7389ed8a4d1e
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Linked notes

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