Dimethylamine → HCID 22637164, compound

HRID 2416082Notes

Reaction equation

HRID 2416082 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][C:29]=1[F:30])[NH:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([O:22][CH2:23][CH3:24])=[C:13]([NH:16][C:17](=[O:21])[CH:18]=[CH:19][CH3:20])[CH:14]=2)[N:9]=[CH:8][C:7]=1[C:25]#[N:26].[CH3:31][NH:32][CH3:33]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][C:29]=1[F:30])[NH:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([O:22][CH2:23][CH3:24])=[C:13]([NH:16][C:17](=[O:21])[CH2:18][CH:19]([N:32]([CH3:33])[CH3:31])[CH3:20])[CH:14]=2)[N:9]=[CH:8][C:7]=1[C:25]#[N:26]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 49823348HCID 49823348, compound

Product 1

HCID 22637164HCID 22637164, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of N-[4-(3-chloro-4-fluoroanilino)-3-cyano-7-ethoxy-6-quinolinyl]-2-butenamide (0.212 g, 0.50 mmol) in 25 ml of 2.0 M dimethylamine in tetrahydrofuran was added 0.02 ml of 40% aqueous Triton B. After 66 h at 25° C. the solution was concentrated, and the residue was partitioned between methylene chloride and water. The residue from the organic layer was dissolved in ether, and the solution was passed onto a pad of hydrous magnesium silicate. The pad was washed with ether and ethyl acetate to give the product as an amber foam after evaporation (0.23 g). Mass spectrum (electrospray, m/e) 469.9 (M+H)+, 235.5 (M+2H)+2.

Workup

  1. concentrationAfter 66 h at 25° C. the solution was concentrated
  2. customthe residue was partitioned between methylene chloride and water
  3. dissolutionThe residue from the organic layer was dissolved in ether
  4. washThe pad was washed with ether and ethyl acetate

Sources & evidence

ORD record
ord-86553ab1b7ab4f06b88786783a5f9efe
Source dataset
uspto-grants-2004_11
Patent number
US06821988B2

Reaction notes

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