Acetic Acid → 1-[1,1-Dimethylethoxycarbonyl]-4-[3-(1-methylpropyl)amino-2-pyridinyl]piperazine

HRID 1449718Notes

Reaction equation

HRID 1449718 reaction equation
[CH3:1][C:2]([CH3:20])([O:4][C:5]([N:7]1[CH2:12][CH2:11][N:10]([C:13]2[C:18]([NH2:19])=[CH:17][CH:16]=[CH:15][N:14]=2)[CH2:9][CH2:8]1)=[O:6])[CH3:3].[CH3:21][C:22](=O)[CH2:23][CH3:24].C(O)(=O)C>CO>[CH3:3][C:2]([CH3:20])([O:4][C:5]([N:7]1[CH2:8][CH2:9][N:10]([C:13]2[C:18]([NH:19][CH:22]([CH3:21])[CH2:23][CH3:24])=[CH:17][CH:16]=[CH:15][N:14]=2)[CH2:11][CH2:12]1)=[O:6])[CH3:1]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 6569Methyl Ethyl KetoneHCID 2756375tert-Butyl 4-(3-aminopyridin-2-yl)piperazine-1-carboxylate

Product 1

HCID 214776321-[1,1-Dimethylethoxycarbonyl]-4-[3-(1-methylpropyl)amino-2-pyridinyl]piperazine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Following the general procedure of PREPARATION 3 and making non-critical variations but starting with 1-[1,1-dimethylethoxycarbonyl]-4-[(3-amino)-2-pyridinyl)piperazine (International Publication No. WO 88/08424, 1.0 g), 2-butanone (0.27 g) sodium cyanoborohydride (0.23 g), acetic acid (5.1 ml) and methanol, the title compound is obtained, NMR (300 MHz, CDCl3) 7.68, 6.94, 6.86, 4.18, 3.56, 3.33, 3.05, 1.53, 1.47, 1.18 and 0.96 δ.

Workup

  1. customthe general procedure of PREPARATION 3

Sources & evidence

ORD record
ord-3e84e5afe812413c868c73466b00b91e
Source dataset
uspto-grants-1997_02
Patent number
US05599930

Reaction notes

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