4-Methylmorpholine → HCID 22466724, compound

HRID 1935143Notes

Reaction equation

HRID 1935143 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]([I:42])[CH:37]=1>C1COCC1>[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]([I:42])[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

6

Reactant 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 685352-Butynoic acidHCID 10110652HCID 10110652, compound

Product 1

HCID 22466724HCID 22466724, compoundYield 38.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Dissolved 275 mg (3.27 mmol) 2-butynoic acid in 20 ml THF under N2 and chilled to 0° C. Added 420 μl (3.23 mmol) isobutyl chloroformate and 355 μl (3.24 mmol) N-methylmorpholine and stirred for 10 minutes. Added dropwise a solution of 500 mg (1.30 mmol) 6-amino-4-[(3-iodophenyl)amino]-3-quinolinecarbonitrile and after 15 minutes, removed ice bath and stirred overnight at 25° C. Stripped solvent, washed with water and collected solids. Boiled in ethyl acetate, collected, and dried in vacuo, giving 228 mg of orange-brown solid: mass spectrum (electrospray m/e): M+H=453.1.

Workup

  1. waitafter 15 minutes
  2. customremoved ice bath
  3. stirringstirred overnight at 25° C
  4. washwashed with water
  5. customcollected solids
  6. customcollected
  7. customdried in vacuo

Sources & evidence

ORD record
ord-0b2b8d03833b41dd8bfd0510e1af981b
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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