4-Methylmorpholine → HCID 22466607, compound

HRID 612237Notes

Reaction equation

HRID 612237 reaction equation
[C:1]([OH:6])(=O)[C:2]#[C:3][CH3:4].CN1CCOCC1.ClC(OCC(C)C)=O.[NH2:22][C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[N:29]=[CH:28][C:27]([C:33]#[N:34])=[C:26]2[NH:35][C:36]1[CH:41]=[CH:40][C:39]([F:42])=[C:38]([F:43])[CH:37]=1>C1COCC1.CN(C=O)C.O>[C:33]([C:27]1[CH:28]=[N:29][C:30]2[C:25]([C:26]=1[NH:35][C:36]1[CH:41]=[CH:40][C:39]([F:42])=[C:38]([F:43])[CH:37]=1)=[CH:24][C:23]([NH:22][C:1](=[O:6])[C:2]#[C:3][CH3:4])=[CH:32][CH:31]=2)#[N:34]

Participants

8

Reactant 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 685352-Butynoic acidHCID 224665706-Amino-4-[(3,4-difluorophenyl)amino]-3-quinolinecarbonitrile

Product 1

HCID 22466607HCID 22466607, compoundYield 60.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Dissolved 425 mg (5.06 mmol) 2-butynoic acid in 40 ml THF and chilled to 0° C. under N2. Added 556 μl (5.06 mmol) N-methylmorpholine and 658 μl (5.06 mmol) isobutyl chloroformate and stirred for 10 minutes. Added dropwise a solution of 1.00 g (3.37 mmol) 6-amino-4-[(3,4-difluorophenyl)amino]-3-quinolinecarbonitrile in 2.0 ml hot DMF and 20 ml THF. Removed ice bath at 15 minutes and stirred at 25° C. overnight. Stripped solvent, slurried residue with water, and collected solids. Boiled in ethyl acetate, collected solids, and dried in vacuo, giving 735 mg of yellow solid: mass spectrum (electrospray m/e): M+H=363.3

Workup

  1. waitRemoved ice bath at 15 minutes
  2. stirringstirred at 25° C. overnight
  3. customcollected solids
  4. customcollected solids
  5. customdried in vacuo

Sources & evidence

ORD record
ord-018a8a295556470184730980059202d9
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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