4-Methylmorpholine → HCID 10135237, compound

HRID 611992Notes

Reaction equation

HRID 611992 reaction equation
ClC(OCC(C)C)=O.CN1CCOCC1.[C:16]([OH:21])(=O)[C:17]#[C:18][CH3:19].[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]([C:42]([F:45])([F:44])[F:43])[CH:37]=1>O1CCCC1>[F:44][C:42]([F:43])([F:45])[C:38]1[CH:37]=[C:36]([NH:35][C:26]2[C:25]3[C:30](=[CH:31][CH:32]=[C:23]([NH:22][C:16](=[O:21])[C:17]#[C:18][CH3:19])[CH:24]=3)[N:29]=[CH:28][C:27]=2[C:33]#[N:34])[CH:41]=[CH:40][CH:39]=1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 685352-Butynoic acidHCID 10131458HCID 10131458, compound

Product 1

HCID 10135237HCID 10135237, compoundYield 46.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Isobutyl chloroformate (1.56 g, 11.4 mmol) and N-methylmorpholine (1.15 g, 11.4 mmol) were added to an ice cold solution of 0.961 g (11.4 mmol) of 2-butynoic acid in 40 mL of tetrahydrofuran under N2. After stirring for 10 min, a solution of 1.50 g (4.57 mmol) of 6-amino-4-[(3-trifluoromethylphenyl)amino]-3-quinolinecarbonitrile in 12 mL of tetrahydrofuran was added dropwise. After stirring at 25° C. overnight, volatile material was removed and the residue was slurried in water and filtered. The crude product was washed 3 times with small portions of hot ethyl acetate and then dried in vacuo (45° C.) to give 0.831 g of yellow solid: mass spectrum (electrospray, m/e): M+H 395.

Workup

  1. stirringAfter stirring at 25° C. overnight
  2. customvolatile material was removed
  3. filtrationfiltered
  4. washThe crude product was washed 3 times with small portions of hot ethyl acetate
  5. customdried in vacuo (45° C.)

Sources & evidence

ORD record
ord-c24ffc1ba4ef4600aad64efef1d40996
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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