Nitrogen → HCID 22466694, compound

HRID 612224Notes

Reaction equation

HRID 612224 reaction equation
ClC(OCC(C)C)=O.[O:9]([CH2:17][C:18]#[C:19][C:20]([OH:22])=O)[Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11].CN1CCOCC1.N#N.[NH2:32][C:33]1[CH:34]=[C:35]2[C:40](=[CH:41][CH:42]=1)[N:39]=[CH:38][C:37]([C:43]#[N:44])=[C:36]2[NH:45][C:46]1[CH:51]=[CH:50][CH:49]=[C:48]([Br:52])[CH:47]=1>O1CCCC1.N1C=CC=CC=1>[Br:52][C:48]1[CH:47]=[C:46]([NH:45][C:36]2[C:35]3[C:40](=[CH:41][CH:42]=[C:33]([NH:32][C:20](=[O:22])[C:19]#[C:18][CH2:17][O:9][Si:10]([C:13]([CH3:14])([CH3:15])[CH3:16])([CH3:11])[CH3:12])[CH:34]=3)[N:39]=[CH:38][C:37]=2[C:43]#[N:44])[CH:51]=[CH:50][CH:49]=1

Participants

8

Reactant 5

HCID 947NitrogenHCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 99677126-Amino-4-(3-bromophenylamino)quinoline-3-carbonitrileHCID 224784454-{[tert-Butyl(dimethyl)silyl]oxy}but-2-ynoic acid

Product 1

HCID 22466694HCID 22466694, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

Isobutyl chloroformate (0.214 g, 1.57 mmol) was dropwise added into an ice cold solution of 4-t-butyldimethylsiloxy-2-butynoic acid (0.336 g, 1.57 mmol) and N-methylmorpholine (0.19 g, 1.88 mmol) in 15 mL of tetrahydrofuan under N2. After stirring for 30 min, the reaction mixture was added dropwise into a solution of 0.4 g (1.18 mmol) of 6-amino-4-[(3-bromophenyl)amino]-3-quinolinecarbonitrile in 3 mL of tetrahydrofuran and 1.5 mL of pyridine and stirred at 0° C. for 1 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 column chromatography eluted with 60% ethyl acetate in hexane. The product was collected, and dried in vacuo to give 0.22 g (35%) of yellow solid;: mass spectrum (electrospray, m/e,): 535.1189 (M+.).

Workup

  1. stirringstirred at 0° C. for 1 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 column chromatography
  7. washeluted with 60% ethyl acetate in hexane
  8. customThe product was collected
  9. customdried in vacuo

Sources & evidence

ORD record
ord-f9c85cc5560a49ad9f2349404c0f5a3b
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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