Sodium hydride → HCID 70873818, compound

HRID 2277423Notes

Reaction equation

HRID 2277423 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[CH2:33][CH:32]([NH2:34])[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[CH2:33][CH:32]([NH:34][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])[CH2:31]1)=[O:29])([CH3:26])([CH3:24])[CH3:25]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1516507Tert-butyl 3-aminoazetidine-1-carboxylateHCID 210819574-Chloro-1-(4-fluorobenzyl)-2-oxo-1,2-dihydro-quinoline-3-carbonitrile

Product 1

HCID 70873818HCID 70873818, 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 (1 eq, 0.250 g, 0.80 mmole) in N,N′-dimethylformamide was added commercially available 3-Amino-azetidine-1-carboxylic acid tert-butyl ester (1.1 eq 0.151 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 3-[3-Cyano-1-(4-fluoro-benzyl)-2-oxo-1,2-dihydro-quinolin-4-ylamino]-azetidine-1-carboxylic acid tert-butyl ester as a pale yellow solid (0.322 g, 90%, calc M+H 449, obs M+H 449).

Workup

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

Sources & evidence

ORD record
ord-7df4d9caa265409fb8f50d65e9ef096d
Source dataset
uspto-grants-2015_09
Patent number
US09133164B2

Reaction notes

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