2-(Methylamino)ethanol → HCID 67202217, compound

HRID 379190Notes

Reaction equation

HRID 379190 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:27][CH3:28])=[C:17]([NH:20][C:21](=[O:26])[CH:22]=[CH:23][CH2:24]Br)[CH:18]=3)[N:13]=[CH:12][C:11]=2[C:29]#[N:30])[CH:5]=[CH:6][C:7]=1[F:8].[CH3:31][NH:32][CH2:33][CH2:34][OH:35]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:27][CH3:28])=[C:17]([NH:20][C:21](=[O:26])[CH:22]=[CH:23][CH2:24][N:32]([CH2:33][CH2:34][OH:35])[CH3:31])[CH:18]=3)[N:13]=[CH:12][C:11]=2[C:29]#[N:30])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 80162-(Methylamino)ethanolHCID 542420754-Bromo-but-2-enoic acid[4-(3-chloro-4-fluoro-phenylamino)-3-cyano-7-methoxy-quinolin-6-yl]-amide

Product 1

HCID 67202217HCID 67202217, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-bromo-but-2-enoic acid[4-(3-chloro-4-fluoro-phenylamino)-3-cyano-7-methoxy-quinolin-6-yl]-amide (250 mg, 0.51 mmol.) and 2-(methylamino)-ethanol(97 mg, 1.02 mmol.) were dissolved with stirring, under nitrogen, in 9 ml anhydrous dimethylformamide. After 48 hours, the mixture was partitioned between saturated sodium bicarbonate solution, and ethyl acetate. The organic phase was seperated, dried over magnesium sulfate, filtered, and evaporated to give a gum. It was chromatographed on silica gel, and eluted with 40/4/1 (ethyl acetate/methanol/triethylamine) producing 183 mg (74%) of the purified product as a yellow solid: mp 210-214° C.

Workup

  1. customthe mixture was partitioned between saturated sodium bicarbonate solution, and ethyl acetate
  2. customThe organic phase was seperated
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customto give a gum
  7. customIt was chromatographed on silica gel
  8. washeluted with 40/4/1 (ethyl acetate/methanol/triethylamine)

Sources & evidence

ORD record
ord-8a8bfa2d301f4ce09b66c337a2ff96f7
Source dataset
uspto-grants-2001_10
Patent number
US06297258B1

Reaction notes

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