3-Chloro-N-[4-(3-chloro-4-fluoroanilino)-3-cyano-7-(4-morpholinyl)-6-quinolinyl]propanamide → N-[4-(3-Chloro-4-fluoroanilino)-3-cyano-7-(4-morpholinyl)-6-quinolinyl]acrylamide

HRID 548505Notes

Reaction equation

HRID 548505 reaction equation
Cl[CH2:2][CH2:3][C:4]([NH:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][C:16]=1[N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)[N:13]=[CH:12][C:11]([C:23]#[N:24])=[C:10]2[NH:25][C:26]1[CH:31]=[CH:30][C:29]([F:32])=[C:28]([Cl:33])[CH:27]=1)=[O:5].CC([O-])(C)C.[K+].CC(O)(C)C>C1COCC1>[Cl:33][C:28]1[CH:27]=[C:26]([CH:31]=[CH:30][C:29]=1[F:32])[NH:25][C:10]1[C:9]2[C:14](=[CH:15][C:16]([N:17]3[CH2:18][CH2:19][O:20][CH2:21][CH2:22]3)=[C:7]([NH:6][C:4](=[O:5])[CH:3]=[CH2:2])[CH:8]=2)[N:13]=[CH:12][C:11]=1[C:23]#[N:24]

Participants

4

Reactant 2

HCID 216973173-Chloro-N-[4-(3-chloro-4-fluoroanilino)-3-cyano-7-(4-morpholinyl)-6-quinolinyl]propanamideHCID 23676527KOtBu tBuOH

Product 1

HCID 11546920N-[4-(3-Chloro-4-fluoroanilino)-3-cyano-7-(4-morpholinyl)-6-quinolinyl]acrylamideYield 101.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3-chloro-N-[4-(3-chloro-4-fluoroanilino)-3-cyano-7-(4-morpholinyl)-6-quinolinyl]propanamide (0.30 g, 0.61 mmol) in 1.2 ml of THF at 0° was added 1.2 ml of 1.0 M KOtBu/tBuOH dropwise during 1 m. After 2 h at 0° the reaction was quenched with solid CO2 and partitioned with DCM-water. The organic layer was washed with water, dried, and evaporated to give 0.28 g of the title compound as a white amorphous solid; ms 452.2 (M+H)+.

Workup

  1. customAfter 2 h at 0° the reaction was quenched with solid CO2
  2. custompartitioned with DCM-water
  3. washThe organic layer was washed with water
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-648f3c3e6c45405cba6f010732edef1b
Source dataset
uspto-grants-2011_05
Patent number
USRE042376E1

Reaction notes

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