Leucinamide → (S)-N-(1-amino-4-methyl-1-oxopentan-2-yl)-3-bromo-8-methyl-6,7,8,9-tetrahydro-5H-imidazo[1,5-a][1,4]diazepine-1-carboxamide

HRID 535970

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]([NH:15][C@@H:16]([CH2:21][CH:22]([CH3:24])[CH3:23])[C:17]([NH:19]C)=[O:18])=[O:14])[N:3]=1.N[C@H](C(N)=O)CC(C)C>>[NH2:19][C:17](=[O:18])[C@@H:16]([NH:15][C:13]([C:4]1[N:3]=[C:2]([Br:1])[N:6]2[CH2:7][CH2:8][CH2:9][N:10]([CH3:12])[CH2:11][C:5]=12)=[O:14])[CH2:21][CH:22]([CH3:24])[CH3:23]

Participants

Reactant 2

HCID 69640Leucinamide

HCID 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 57635701(S)-N-(1-amino-4-methyl-1-oxopentan-2-yl)-3-bromo-8-methyl-6,7,8,9-tetrahydro-5H-imidazo[1,5-a][1,4]diazepine-1-carboxamide

Procedure

This intermediate was prepared following the synthesis of (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-carboxamide (intermediate 55B) by replacing H-Leu-NHMe with Leucine amide 59A (Chem-Impex). LCMS (+ESI) m/z 386.1 [M+H]+.

Workup

customThis intermediate was prepared

Sources & evidence

ORD record: ord-bbeb408296034a11b081eaa99389fa76
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859538B2

Linked notes

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