4-Methylmorpholine → HCID 10114657, 화합물

HRID 1935132노트

반응식

HRID 1935132 반응식
ClC(OCC(C)C)=O.[CH3:9][N:10]([CH3:17])[CH2:11][C:12]#[C:13][C:14](O)=[O:15].CN1CCOCC1.[NH2:25][C:26]1[CH:27]=[C:28]2[C:33](=[CH:34][CH:35]=1)[N:32]=[CH:31][C:30]([C:36]#[N:37])=[C:29]2[NH:38][C:39]1[CH:44]=[CH:43][CH:42]=[C:41]([Br:45])[CH:40]=1>N1C=CC=CC=1>[Br:45][C:41]1[CH:40]=[C:39]([NH:38][C:29]2[C:28]3[C:33](=[CH:34][CH:35]=[C:26]([NH:25][C:14](=[O:15])[C:13]#[C:12][CH2:11][N:10]([CH3:17])[CH3:9])[CH:27]=3)[N:32]=[CH:31][C:30]=2[C:36]#[N:37])[CH:44]=[CH:43][CH:42]=1

참가 물질

6

반응물 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 99677126-Amino-4-(3-bromophenylamino)quinoline-3-carbonitrileHCID 150797524-(Dimethylamino)but-2-ynoic acid

생성물 1

HCID 10114657HCID 10114657, 화합물수율 21%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

Isobutyl chloroformate (0.342 g, 2.5 mmol) was dropwise added into an ice cold solution of 4-dimethylamino-2-butynoic acid (0.9 g, 3.8 mmol) and N-methyl-morpholine (0.384 g, 3.8mmol) in 50 mL of tetrahydrofaan under N2. After stirring for 30 min, a solution of 0.644 g (1.9 mmol) of 6-amino-4-[(3-bromophenyl)amino]-3-quinolinecarbonitrile in 10 mL of pyridine was added dropwise and the mixture was stirred at 0° C. for 2.5 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 15% methanol in ethyl acetate. The product was collected, and dried in vacuo to give 0.144 g (21%) of yellow solid; mass spectrum (electrospray, m/e,): 447.9, 450.2 (M+H+); mp 180° C. (dec.).

후처리

  1. stirringthe mixture was stirred at 0° C. for 2.5 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 15% methanol in ethyl acetate
  8. customThe product was collected
  9. customdried in vacuo

출처 및 근거

ORD 기록
ord-e773faacd1df47728ea986284c5107c4
출처 데이터셋
uspto-grants-2002_05
특허 번호
US06384051B1

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