5-chloro-1-methyl-4-nitro-1H-pyrazole → tert-butyl (4-(1-methyl-4-nitro-1H-pyrazol-5-yl)morpholin-2-yl)methylcarbamate

HRID 2089451Notes

Reaction equation

HRID 2089451 reaction equation
Cl[C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[NH:11]1[CH2:16][CH2:15][O:14][CH:13]([CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:12]1>>[CH3:7][N:6]1[C:2]([N:11]2[CH2:16][CH2:15][O:14][CH:13]([CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:23])([CH3:22])[CH3:24])[CH2:12]2)=[C:3]([N+:8]([O-:10])=[O:9])[CH:4]=[N:5]1

Participants

3

Reactant 2

HCID 123448365-chloro-1-methyl-4-nitro-1H-pyrazoleHCID 19081107tert-Butyl [(morpholin-2-yl)methyl]carbamate

Product 1

HCID 58464977tert-butyl (4-(1-methyl-4-nitro-1H-pyrazol-5-yl)morpholin-2-yl)methylcarbamateYield 93%

Procedure

Reaction of 5-chloro-1-methyl-4-nitro-1H-pyrazole and tert-butyl morpholin-2-ylmethylcarbamate gave tert-butyl (4-(1-methyl-4-nitro-1H-pyrazol-5-yl)morpholin-2-yl)methylcarbamate as a yellow oil (196 mg, 93%). 1H NMR (400 MHz, CDCl3) δ 8.04 (s, 1H), 4.92 (s br, 1H), 4.00 (dd, J=11.3, 2.9 Hz, 1H), 3.90-3.68 (m, 5H), 3.57 (td, J=11.6, 3.2 Hz, 1H), 3.38-3.24 (m, 2H), 3.15 (ddd, J=14.1, 7.1, 5.1 Hz, 1H), 2.86 (d, J=11.8 Hz, 1H), 2.77 (d, J=11.8 Hz, 1H), 1.45 (s, 9H)

Sources & evidence

ORD record
ord-e05ede1f23474a1d976e13fe4f45ef24
Source dataset
uspto-grants-2013_05
Patent number
US08436001B2

Reaction notes

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