4-Methylmorpholine → HCID 22466605, compound

HRID 1935148Notes

Reaction equation

HRID 1935148 reaction equation
[C:1]([OH:6])(=O)[C:2]#[C:3][CH3:4].ClC(OCC(C)C)=O.CN1CCOCC1.[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][CH:39]=[C:38]([CH:42]([CH3:44])[CH3:43])[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][CH:39]=[C:38]([CH:42]([CH3:43])[CH3:44])[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 22466682HCID 22466682, compound

Product 1

HCID 22466605HCID 22466605, compoundYield 27%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Dissolved 695 mg (8.27 mmol) 2-butynoic acid in 40 ml THF and chilled to 0° C. under N2. Added 1.08 ml (8.30 mmol) isobutyl chloroformate and 910 μl (8.27 mmol) N-methylmorpholine and stirred for 10 minutes. Dropwise added a solution of 1.00 g (3.31 mmol) 6-amino-4-[(3-isopropylphenyl)amino]-3-quinolinecarbonitrile in 2.0 ml DMF and 15 ml THF. Removed ice bath at 15 minutes and stirred at 25° C. overnight. Stripped solvent, slurried residue with water, and collected solid. Recrystallized from ethyl acetate and dried in vacuo, giving 329 mg of yellow-green solid: mass spectrum (electrospray m/e): M+H=369.2.

Workup

  1. waitRemoved ice bath at 15 minutes
  2. stirringstirred at 25° C. overnight
  3. customcollected solid
  4. customRecrystallized from ethyl acetate
  5. customdried in vacuo

Sources & evidence

ORD record
ord-14f148e82efc4880822160c7b2e873fe
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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