5-chloro-1-methyl-4-nitro-1H-pyrazole → (R)-tert-butyl 4-(4-amino-1-methyl-1H-pyrazol-5-yl)-3-ethylpiperazine-1-carboxylate

HRID 1915760Notes

Reaction equation

HRID 1915760 reaction equation
Cl[C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[N+:8]([O-])=O.[CH2:11]([C@H:13]1[NH:18][CH2:17][CH2:16][N:15]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:14]1)[CH3:12]>>[NH2:8][C:3]1[CH:4]=[N:5][N:6]([CH3:7])[C:2]=1[N:18]1[CH2:17][CH2:16][N:15]([C:19]([O:21][C:22]([CH3:24])([CH3:23])[CH3:25])=[O:20])[CH2:14][C@H:13]1[CH2:11][CH3:12]

Participants

3

Reactant 2

HCID 123448365-chloro-1-methyl-4-nitro-1H-pyrazoleHCID 24820337(R)-1-Boc-3-Ethylpiperazine

Product 1

HCID 86679973(R)-tert-butyl 4-(4-amino-1-methyl-1H-pyrazol-5-yl)-3-ethylpiperazine-1-carboxylate

Procedure

Following the procedure for Intermediate 10 starting from 5-chloro-1-methyl-4-nitro-1H-pyrazole from Example 1 and (R)-tert-butyl 3-ethylpiperazine-1-carboxylate gave (R)-tert-butyl 4-(4-amino-1-methyl-1H-pyrazol-5-yl)-3-ethylpiperazine-1-carboxylate as an orange gum (118 mg, 67% over two steps). LCMS (ES+) m/z 310 (M+1).

Sources & evidence

ORD record
ord-16bf9659209141c695e17a2f989a4e4b
Source dataset
uspto-grants-2013_12
Patent number
US08614206B2

Reaction notes

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