Water → 4-(2,2-Difluoro-benzo[1,3]dioxol-5-ylmethyl)-piperazine-1-carboxylic acid pyridin-3-ylamide

HRID 1429679Notes

Reaction equation

HRID 1429679 reaction equation
C1(O[C:8](=[O:16])[NH:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)C=CC=CC=1.[F:17][C:18]1([F:34])[O:22][C:21]2[CH:23]=[CH:24][C:25]([CH2:27][N:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)=[CH:26][C:20]=2[O:19]1.O>CS(C)=O>[N:12]1[CH:13]=[CH:14][CH:15]=[C:10]([NH:9][C:8]([N:31]2[CH2:32][CH2:33][N:28]([CH2:27][C:25]3[CH:24]=[CH:23][C:21]4[O:22][C:18]([F:34])([F:17])[O:19][C:20]=4[CH:26]=3)[CH2:29][CH2:30]2)=[O:16])[CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6935890Phenyl pyridin-3-ylcarbamateHCID 66553702Difluoromethylenedioxybenzylpiperazine

Product 1

HCID 578808834-(2,2-Difluoro-benzo[1,3]dioxol-5-ylmethyl)-piperazine-1-carboxylic acid pyridin-3-ylamideYield 84%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of pyridine-3-yl-carbamic acid phenyl ester (9.08 g, 42.4 mmol) in DMSO (84 mL) was added 1-(2,2-difluoro-benzo[1,3]dioxol-5-ylmethyl)-piperazine (11.4 g, 44.5 mmol). The reaction mixture was stirred at room temperature for 16 h, then treated with water (130 mL). The resulting solid was isolated by filtration, rinsed with water (4×50 mL) and dried under vacuum. The solid was recrystallized (EtOH—H2O) to give 4-(2,2-difluoro-benzo[1,3]dioxol-5-ylmethyl)-piperazine-1-carboxylic acid pyridin-3-ylamide (13.4 g, 84%). MS (ESI+): calcd for C18H18F2N4O3 m/z 376.13. found 377.1 (M+H)+. 1H NMR (CDCl3): 8.46 (d, J=2.5 Hz, 1H), 8.23-8.21 (m, 1H), 7.99-7.96 (m, 1H), 7.22-7.19 (m, 2H), 7.11 (s, 1H), 6.99-6.98 (m, 2H), 3.54-3.52 (m, 4H), 3.49 (s, 2H, 2.46-2.44 (m, 4H).

Workup

  1. customThe resulting solid was isolated by filtration
  2. washrinsed with water (4×50 mL)
  3. customdried under vacuum
  4. customThe solid was recrystallized (EtOH—H2O)

Sources & evidence

ORD record
ord-cf17dbc3c31c46cea7bd5456ef10c706
Source dataset
uspto-grants-2015_01
Patent number
US08940745B2

Reaction notes

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