(R)-1-Boc-3-methylpiperazine → HCID 86679989, compound

HRID 1915777Notes

Reaction equation

Cl[C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)[N:5]=[CH:4][C:3]=1[N+:16]([O-])=O.[CH3:19][C@H:20]1[NH:25][CH2:24][CH2:23][N:22]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:21]1>>[NH2:16][C:3]1[CH:4]=[N:5][N:6]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)[C:2]=1[N:25]1[CH2:24][CH2:23][N:22]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:21][C@H:20]1[CH3:19]

Participants

Reactant 2

HCID 2756811(R)-1-Boc-3-methylpiperazine

HCID 86679988HCID 86679988, compound

Product 1

HCID 86679989HCID 86679989, compound

Procedure

Following the procedure for Intermediate 33 starting with 5-chloro-1-(4-methoxybenzyl)-4-nitro-1H-pyrazole and (R)-tert-butyl 3-methylpiperazine-1-carboxylate gave (R)-tert-butyl 4-(4-amino-1-(4-methoxybenzyl)-1H-pyrazol-5-yl)-3-methylpiperazine-1-carboxylate as a red gum (325 mg, 81% over two steps). 1H NMR (400 MHz, CDCl3) δ 7.16-7.11 (m, 3H), 6.82 (d, J=8.6 Hz, 2H), 5.16 (d, J=14.8 Hz, 1H), 5.05 (d, J=14.8 Hz, 1H), 4.10-3.80 (m, 2H), 3.78 (s, 3H), 3.26-3.19 (m, 1H), 3.01 (td, J=11.4, 3.0 Hz, 1H), 2.86 (t, J=13.2 Hz, 1H), 2.66 (s, 2H), 2.57 (s, 2H), 1.47 (s, 9H), 0.81 (d, J=6.3 Hz, 3H).

Sources & evidence

ORD record: ord-0c0a5311e2f646a095db5717fc302c1c
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08614206B2

Reaction notes

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