Ammonia → 2-[2-(4-Methyl-piperazin-1-yl)-5-nitro-pyridin-4-yl]-acetamide

HRID 1992650Notes

Reaction equation

C([O:3][C:4](=O)[CH2:5][C:6]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][N:9]=[C:8]([N:15]2[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]2)[CH:7]=1)C.[NH3:23]>CO>[CH3:21][N:18]1[CH2:19][CH2:20][N:15]([C:8]2[CH:7]=[C:6]([CH2:5][C:4]([NH2:23])=[O:3])[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][N:9]=2)[CH2:16][CH2:17]1

Participants

Conditions

Temperature: 40 °C

Procedure

[2-(4-Methyl-piperazin-1-yl)-5-nitro-pyridin-4-yl]-acetic acid ethyl ester (250 mg, 0.81 mmol) is dissolved in methanol (2.5 ml). An aqueous solution of ammonia (25%, 2.5 ml) is added, and the mixture is warmed to 40° C. for 18 h. TLC analysis indicated complete conversion of the starting material. Solvents are removed, and the residue is purified by FCC (CH2Cl2/MeOH, gradient from 97:3 to 90:10) to afford the title compound. 1H NMR (d6-DMSO, 400 MHz): δ 2.21 (s, 3H), 2.38 (m, 4H), 3.72 (m, 4H), 3.80 (s, 2H), 6.84 (s, 1H), 6.93 (s, broad, 1H), 7.46 (s, broad, 1H), 8.85 (s, 1H). ES+−MS: 280.3 [M+H]+, ES−−MS: 278.3 [M−H]−.

Workup

customSolvents are removed
customthe residue is purified by FCC (CH2Cl2/MeOH, gradient from 97:3 to 90:10)

Sources & evidence

ORD record: ord-731529788c804ff4a893cd0cc13ea078
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07648989B2

Reaction notes

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