Sodium hydride → HCID 70873821, compound

HRID 2277426Notes

Reaction equation

HRID 2277426 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[C:4](=[O:20])[C:3]=1[C:21]#[N:22].[C:23]([O:27][C:28]([N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)=[O:29])([CH3:26])([CH3:25])[CH3:24].[H-].[Na+]>CN(C=O)C>[C:23]([O:27][C:28]([N:30]1[CH2:35][CH2:34][N:33]([C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[C:4](=[O:20])[C:3]=2[C:21]#[N:22])[CH2:32][CH2:31]1)=[O:29])([CH3:26])([CH3:24])[CH3:25]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 143452tert-Butyl piperazine-1-carboxylateHCID 210819574-Chloro-1-(4-fluorobenzyl)-2-oxo-1,2-dihydro-quinoline-3-carbonitrile

Product 1

HCID 70873821HCID 70873821, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 4-Chloro-1-(4-fluoro-benzyl)-2-oxo-1,2-dihydro-quinoline-3-carbonitrile, compound C, (1 eq, 0.250 g, 0.80 mmole) in N,N′-dimethylformamide was added commercially available piperazine-1-carboxylic acid tert-butyl ester (1.1 eq, 0.164 g, 0.88 mmole) and treated with 60% NaH oil dispersion (1.5 eq, 0.029 g, 1.2 mmole). After stirring for 2 h, reaction was quenched with 10% HCl aq, (1 ml) then H2O (5 ml), A solid formed that was collected and dried. No further purification was necessary, afforded 4-[3-Cyano-1-(4-fluoro-benzyl)-2-oxo-1,2-dihydro-quinolin-4-yl]-piperazine-1-carboxylic acid tert-butyl ester as a pale yellow solid (0.325 g, 88%, calc M+H 463, obs M+H 463).

Workup

  1. customreaction
  2. customwas quenched with 10% HCl aq, (1 ml)
  3. customH2O (5 ml), A solid formed that
  4. customwas collected
  5. customdried
  6. customNo further purification

Sources & evidence

ORD record
ord-ba24ba5849d04f6688450fc2b011c94a
Source dataset
uspto-grants-2015_09
Patent number
US09133164B2

Reaction notes

Loading…