Dimethylamine → (s)-3-Bromo-n-(1-(dimethylamino)-3,3-dimethyl-1-oxobutan-2-yl)-8-methyl-6,7,8,9-tetrahydro-5h-imidazo[1,5-a][1,4]diazepine-1-carboxamide

HRID 2110235

Reaction equation

HRID 2110235 reaction equation
[Br:1][C:2]1[N:6]2[CH2:7][CH2:8][CH2:9][N:10]([CH3:12])[CH2:11][C:5]2=[C:4]([C:13](N[C@@H](CC(C)C)C(NC)=O)=[O:14])[N:3]=1.[NH2:25][C@H:26]([C:31]([OH:33])=O)[C:27]([CH3:30])([CH3:29])[CH3:28].[CH3:34][NH:35][CH3:36]>C1COCC1>[Br:1][C:2]1[N:6]2[CH2:7][CH2:8][CH2:9][N:10]([CH3:12])[CH2:11][C:5]2=[C:4]([C:13]([NH:25][C@@H:26]([C:27]([CH3:30])([CH3:29])[CH3:28])[C:31]([N:35]([CH3:36])[CH3:34])=[O:33])=[O:14])[N:3]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 164608L-tert-LeucineHCID 57635259(S)-3-bromo-8-methyl-N-(4-methyl-1-(methylamino)-1-oxopentan-2-yl)-6,7,8,9-tetrahydro-5H-imidazo[1,5-a][1,4]diazepine-1-carboxamide2×

Product 1

HCID 57635558(s)-3-Bromo-n-(1-(dimethylamino)-3,3-dimethyl-1-oxobutan-2-yl)-8-methyl-6,7,8,9-tetrahydro-5h-imidazo[1,5-a][1,4]diazepine-1-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

This intermediate was prepared following the synthesis of ((S)-N-(1-amino-3,3-dimethyl-1-oxobutan-2-yl)-3-bromo-8-methyl-6,7,8,9-tetrahydro-5H-imidazo[1,5-a][1,4]diazepine-1-carboxamide (Intermediate 55B) by replacing Z-Leu-OH with tert-Leu-OH, and replacing methylamine hydrochloride with dimethylamine solution in THF. LCMS (+ESI) m/z 417.1 [M+H]+.

Workup

  1. customThis intermediate was prepared

Sources & evidence

ORD record
ord-fe4d9ef68c2044a28c38648b1d1dea77
Source dataset
uspto-grants-2009_04
Patent number
US07517874B2

Linked notes

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