5-bromo-1-methyl-4-nitro-1H-pyrazole → tert-butyl 4-(1-methyl-4-nitro-1H-pyrazol-5-yl)-5-oxo-1,4-diazepane-1-carboxylate

HRID 1915805Notes

Reaction equation

HRID 1915805 reaction equation
Br[C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[O:11]=[C:12]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14][NH:13]1>>[CH3:7][N:6]1[C:2]([N:13]2[C:12](=[O:11])[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)=[C:3]([N+:8]([O-:10])=[O:9])[CH:4]=[N:5]1

Participants

3

Reactant 2

HCID 12795875-bromo-1-methyl-4-nitro-1H-pyrazoleHCID 226177365-Oxo-(1,4)diazepane-1-carboxylic acid tert-butyl ester

Product 1

HCID 86680013tert-butyl 4-(1-methyl-4-nitro-1H-pyrazol-5-yl)-5-oxo-1,4-diazepane-1-carboxylateYield 33%

Procedure

Following the procedure for Intermediate 202 starting from 5-bromo-1-methyl-4-nitro-1H-pyrazole and tert-butyl 5-oxo-1,4-diazepane-1-carboxylate gave tert-butyl 4-(1-methyl-4-nitro-1H-pyrazol-5-yl)-5-oxo-1,4-diazepane-1-carboxylate as a brown gum (136 mg, 33%). 1H NMR (400 MHz, d4-MeOD) δ 8.18 (s, 1H), 4.04-3.72 (m, 5H), 3.90-3.62 (m, 4H), 3.02-2.86 (m, 2H), 1.52 (s, 9H).

Sources & evidence

ORD record
ord-e7af3e9c098a466b99c4509037fa249c
Source dataset
uspto-grants-2013_12
Patent number
US08614206B2

Reaction notes

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