Sodium Chloride → HCID 54256437, compound

HRID 612132Notes

Reaction equation

HRID 612132 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:21][CH3:22])=[C:17]([NH2:20])[CH:18]=3)[N:13]=[CH:12][C:11]=2[C:23]#[N:24])[CH:5]=[CH:6][C:7]=1[F:8].CCN(C(C)C)C(C)C.Br[CH2:35]/[CH:36]=[CH:37]/[C:38](Cl)=[O:39].[Cl-].[Na+].[NH:43]1[CH2:48][CH2:47][O:46][CH2:45][CH2:44]1.C(=O)(O)[O-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:21][CH3:22])=[C:17]([NH:20][C:38](=[O:39])[CH:37]=[CH:36][CH2:35][N:43]4[CH2:48][CH2:47][O:46][CH2:45][CH2:44]4)[CH:18]=3)[N:13]=[CH:12][C:11]=2[C:23]#[N:24])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

8

Reactant 6

HCID 5234Sodium ChlorideHCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 111424366-Amino-4-(3-chloro-4-fluoro-phenylamino)-7-methoxy-quinoline-3-carbonitrileHCID 11263885(E)-4-Bromo-2-butenoyl Chloride

Product 1

HCID 54256437HCID 54256437, compoundYield 47.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a mixture of 1.2 g (3.5 mmol) of 4-[(3-chloro-4-fluorophenyl)amino]-7-methoxy-6-amino-quinoline-3-carbonitrile and 2.44 ml (14 mmol) of Hunig's base in 50 ml of dry THF at 0° C., with stirring, was added a THF solution containing 2.57 g (14 mmol) of 4-bromo crotonyl chloride dropwise. The mixture was stirred for an additional hour at 0° C. 50 ml of saturated sodium chloride solution was added to the reaction mixture, then it was extracted with ethyl acetate. The ethyl acetate solution was dried over sodium sulfate and then was added to a solution of 4.58 ml (52.5 mmol) morpholine in mL of THF at 0° C. dropwise. The solution was stirred an overnight at 0° C. The mixture was poured into diluted sodium bicarbonate solution. The organic layer dried over sodium sulfate. Chromatography gave 0.83 grams off-white solid: mass spectrum (electrospray, m/e): M+H 496.0.

Workup

  1. stirringThe mixture was stirred for an additional hour at 0° C
  2. extractionit was extracted with ethyl acetate
  3. dry with materialThe ethyl acetate solution was dried over sodium sulfate
  4. stirringThe solution was stirred an overnight at 0° C
  5. dry with materialThe organic layer dried over sodium sulfate

Sources & evidence

ORD record
ord-8ae6853c50124bc08545bb3984c906f0
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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