Water → HCID 22466587, compound

HRID 1934991Notes

Reaction equation

HRID 1934991 reaction equation
ClC([O:4][CH2:5][CH:6]([CH3:8])C)=O.[CH3:9]N1CCOCC1.[NH2:16][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[N:23]=[CH:22][C:21]([C:27]#[N:28])=[C:20]2[NH:29][C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([O:36][CH3:37])[CH:31]=1.O>C1COCC1.CN(C=O)C>[C:27]([C:21]1[CH:22]=[N:23][C:24]2[C:19]([C:20]=1[NH:29][C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([O:36][CH3:37])[CH:31]=1)=[CH:18][C:17]([NH:16][C:5](=[O:4])[C:6]#[C:8][CH3:9])=[CH:26][CH:25]=2)#[N:28]

Participants

7

Reactant 4

HCID 962WaterHCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 22466726HCID 22466726, compound

Product 1

HCID 22466587HCID 22466587, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Dissolved 362 mg (4.31 mmol) acid in 20 ml THF under N2 and chilled to 0° C. Added 560 μl (4.30 mmol) isobutyl chloroformate and 475 μl (4.31 mmol) N-methylmorpholine and stirred for 10 minutes. Dissolved 500 mg (1.72 mmol) 6-amino-4-[(3-methoxyphenyl)amino]-3-quinolinecarbonitrile in 2 ml hot DMF and added 10 ml THF. Added this to the mixed anhydride dropwise, stirred for 15 minutes at 0° C. and at 25° C. overnight. Stripped solvent, slurried residue with water, collected solids, and air dried. Recrystallized from ethyl acetate and dried in vacuo, giving 270 mg of yellow solid: mass spectrum (electrospray m/e): M+H=357.1.

Workup

  1. stirringstirred for 15 minutes at 0° C. and at 25° C. overnight
  2. customcollected solids, and air
  3. customdried
  4. customRecrystallized from ethyl acetate
  5. customdried in vacuo

Sources & evidence

ORD record
ord-453678834b8a49f888aa3982db3ba4d9
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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