(R)-1-Boc-3-methylpiperazine → HCID 86679983, compound

HRID 1915772Notes

Reaction equation

HRID 1915772 reaction equation
Cl[C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[N+:8]([O-])=O.[CH3:11][C@H:12]1[NH:17][CH2:16][CH2:15][N:14]([C:18](OC(C)(C)C)=O)[CH2:13]1>>[CH3:11][C@@H:12]1[CH2:13][N:14]([CH3:18])[CH2:15][CH2:16][N:17]1[C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[NH2:8]

Participants

3

Reactant 2

HCID 2756811(R)-1-Boc-3-methylpiperazineHCID 123448365-chloro-1-methyl-4-nitro-1H-pyrazole

Product 1

HCID 86679983HCID 86679983, compound

Procedure

Following the procedure for Intermediate 23 starting with 5-chloro-1-methyl-4-nitro-1H-pyrazole from Example 1 and (R)-tert-butyl 3-methyl-piperazine-1-carboxylate gave (R)-5-(2,4-dimethylpiperazin-1-yl)-1-methyl-1H-pyrazol-4-amine as a brown solid (94 mg, 62% over four steps). 1H NMR (400 MHz, CDCl3) δ 7.07 (s, 1H), 3.66 (s, 3H), 3.59-3.44 (m, 2H), 2.99-2.86 (m, 3H), 2.46-2.31 (m, 4H), 2.03 (t, J=10.7 Hz, 1H), 0.87 (d, J=6.3 Hz, 3H). Exchangeable NH2 not observed.

Sources & evidence

ORD record
ord-f4a4acbccf8e4d83a9946797658abc9f
Source dataset
uspto-grants-2013_12
Patent number
US08614206B2

Reaction notes

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