Ammonium Hydroxide → 2-[5-(4-Methyl-piperazin-1-yl)-pyridin-3-yl]-acetamide

HRID 1992635Notes

Reaction equation

HRID 1992635 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[C:10]([CH2:14][C:15]([OH:17])=O)[CH:11]=[N:12][CH:13]=2)[CH2:4][CH2:3]1.C(C1NC=CN=1)(C1[NH:21]C=CN=1)=O.[NH4+].[OH-]>CN(C=O)C>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[C:10]([CH2:14][C:15]([NH2:21])=[O:17])[CH:11]=[N:12][CH:13]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 66869047[5-(4-Methyl-piperazin-1-yl)-pyridin-3-yl]-acetic acid

Product 1

HCID 668692842-[5-(4-Methyl-piperazin-1-yl)-pyridin-3-yl]-acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

[5-(4-Methyl-piperazin-1-yl)-pyridin-3-yl]-acetic acid (1.57 g, 5.78 mmol) and carbonyl diimidazole (1.03 g, 6.36 mmol) are dissolved under an atmosphere of argon in DMF (16 ml). After stirring at RT for 1 h, aqueous NH4OH (25%, 16 ml) is added, and stirring at RT is continued for 15 minutes. TLC analysis indicated complete consumption of starting material. The aqueous layer is saturated with NaCl and extracted repeatedly with CH2Cl2. The organic layers are dried over Na2SO4 and concentrated. Purification by FCC (CH2Cl2:MeOH 95:5 to 90:10 to 80:20 to 70:30 to 50:50 to 25:75 to 0:100) yields the title compound. 1H NMR (d6-DMSO 400 MHz): δ 2.76 (s, 3H), 3.12-3.42 (m, 8H), 3.34 (s, 2H), 6.86-6.96 (br s, 1H), 7.26 (s, 1H), 7.93 (s, 1H), 8.21 (s, 1H). ES+−MS: 235.4 [M+H]+.

Workup

  1. stirringstirring at RT
  2. waitis continued for 15 minutes
  3. customconsumption of starting material
  4. extractionextracted repeatedly with CH2Cl2
  5. dry with materialThe organic layers are dried over Na2SO4
  6. concentrationconcentrated
  7. customPurification by FCC (CH2Cl2:MeOH 95:5 to 90:10 to 80:20 to 70:30 to 50:50 to 25:75 to 0:100)

Sources & evidence

ORD record
ord-b6274356b31940ffa0ad858556d84a21
Source dataset
uspto-grants-2010_01
Patent number
US07648989B2

Reaction notes

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