Sodium hydride → HCID 70874243, compound

HRID 2277433Notes

Reaction equation

HRID 2277433 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([CH2:12][CH2:13][O:14][CH2:15][CH3:16])[C:4](=[O:17])[C:3]=1[C:18]#[N:19].[C:20]([O:24][C:25]([N:27]1[CH2:30][CH:29]([NH2:31])[CH2:28]1)=[O:26])([CH3:23])([CH3:22])[CH3:21].[H-].[Na+]>>[C:20]([O:24][C:25]([N:27]1[CH2:30][CH:29]([NH:31][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]([CH2:12][CH2:13][O:14][CH2:15][CH3:16])[C:4](=[O:17])[C:3]=2[C:18]#[N:19])[CH2:28]1)=[O:26])([CH3:23])([CH3:21])[CH3:22]

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 1516507Tert-butyl 3-aminoazetidine-1-carboxylateHCID 70914022HCID 70914022, compound

Product 1

HCID 70874243HCID 70874243, compound

Procedure

To a stirred solution of 4-Chloro-1-(2-ethoxy-ethyl)-2-oxo-1,2-dihydro-quinoline-3-carbonitrile (1 eq, 0.100 g, 0.36 mmole) in N,N′-dimethylfomamide was added commercially available 3-Amino-azetidine-1-carboxylic acid tert-butyl ester (1.1 eq, 0.068 g, 0.39 mmole) and treated with 60% NaH oil dispersion (1.5 eq, 0.013 g, 0.54 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-(2-ethoxy-ethyl)-2-oxo-1,2-dihydro-quinolin-4-ylamino]-azetidine-1-carboxylic acid tert-butyl ester as a pale yellow solid (0.133 g, 90%, calc M+H 413, obs M+H 413).

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-06e2cd66ee3845a59e6ab09b95884e0e
Source dataset
uspto-grants-2015_09
Patent number
US09133164B2

Reaction notes

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