4-Methylmorpholine → HCID 10884588, compound

HRID 1935133Notes

Reaction equation

HRID 1935133 reaction equation
ClC(OCC(C)C)=O.[CH3:9][O:10][CH2:11][C:12]#[C:13][C:14]([OH:16])=O.CN1CCOCC1.[NH2:24][C:25]1[CH:26]=[C:27]2[C:32](=[CH:33][CH:34]=1)[N:31]=[CH:30][C:29]([C:35]#[N:36])=[C:28]2[NH:37][C:38]1[CH:43]=[CH:42][CH:41]=[C:40]([Br:44])[CH:39]=1>O1CCCC1.N1C=CC=CC=1>[Br:44][C:40]1[CH:39]=[C:38]([NH:37][C:28]2[C:27]3[C:32](=[CH:33][CH:34]=[C:25]([NH:24][C:14](=[O:16])[C:13]#[C:12][CH2:11][O:10][CH3:9])[CH:26]=3)[N:31]=[CH:30][C:29]=2[C:35]#[N:36])[CH:43]=[CH:42][CH:41]=1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 99677126-Amino-4-(3-bromophenylamino)quinoline-3-carbonitrileHCID 111262132-Butynoic acid, 4-methoxy-

Product 1

HCID 10884588HCID 10884588, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

Isobutyl chloroformate (0.432 g, 3.2 mmol) was dropwise added into an ice cold solution of 4-methoxy-2-butynoic acid (0.72 g, 6.32 mmol) and N-methylmorpholine (0.959 g, 9.78 mmol) in 20 mL of tetrahydrofuran under N2. After stirring for 30 min, a solution of 0.5 g (1.58 mmol) of 6-amino-4-[(3-bromophenyl)amino]-3-quinolinecarbonitrile in 8 mL of pyridine was added dropwise and the mixture was stirred at 0° C. for 2 hr. The reaction was quenched with ice water, poured into saturated sodium bicarbonate and brine, and extracted with ethyl acetate. The ethyl acetate layer was concentrated and purified by thin-layer chromatography eluted with 5% methanol in chlorform. The product was collected, and dried in vacuo to give 0.27 g (41%) of yellow solid; mass spectrum (electrospray, m/e,): 435.1, 437.0 (M+H+); mp 197° C. (dec.).

Workup

  1. stirringthe mixture was stirred at 0° C. for 2 hr
  2. customThe reaction was quenched with ice water
  3. additionpoured into saturated sodium bicarbonate and brine
  4. extractionextracted with ethyl acetate
  5. concentrationThe ethyl acetate layer was concentrated
  6. custompurified by thin-layer chromatography
  7. washeluted with 5% methanol in chlorform
  8. customThe product was collected
  9. customdried in vacuo

Sources & evidence

ORD record
ord-d2965f1ba47a4e43bab12dff548c8e50
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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