Nitrogen → HCID 10884588, compound

HRID 612223Notes

Reaction equation

HRID 612223 reaction equation
ClC(OCC(C)C)=O.[CH3:9][O:10][CH2:11][C:12]#[C:13][C:14]([OH:16])=O.CN1CCOCC1.N#N.[NH2:26][C:27]1[CH:28]=[C:29]2[C:34](=[CH:35][CH:36]=1)[N:33]=[CH:32][C:31]([C:37]#[N:38])=[C:30]2[NH:39][C:40]1[CH:45]=[CH:44][CH:43]=[C:42]([Br:46])[CH:41]=1>N1C=CC=CC=1>[Br:46][C:42]1[CH:41]=[C:40]([NH:39][C:30]2[C:29]3[C:34](=[CH:35][CH:36]=[C:27]([NH:26][C:14](=[O:16])[C:13]#[C:12][CH2:11][O:10][CH3:9])[CH:28]=3)[N:33]=[CH:32][C:31]=2[C:37]#[N:38])[CH:45]=[CH:44][CH:43]=1

Participants

7

Reactant 5

HCID 947NitrogenHCID 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 1

HCID 1049PyridineSolvent

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 tetrahydrofuan 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-bb87a98b77d34cc7ab4ff822e23d43f7
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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