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4-Methylmorpholine → N-{3-Cyano-[(3-methylphenyl)amino]-6-quinolinyl}-2-butynamide

HRID 612069
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인쇄 미리보기

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HRID 612069 반응식
[C:1]([OH:6])(=O)[C:2]#[C:3][CH3:4].ClC(O[CH2:11][CH:12]([CH3:14])[CH3:13])=O.C[N:16]1CCO[CH2:18][CH2:17]1.[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]2NC1C=CC=C(C)C=1.[CH2:43]1COCC1>O>[C:33]([C:27]1[C:28]([NH:16][C:17]2[CH:18]=[CH:43][CH:13]=[C:12]([CH3:14])[CH:11]=2)=[N:29][C:30]2[C:25]([CH:26]=1)=[CH:24][C:23]([NH:22][C:1](=[O:6])[C:2]#[C:3][CH3:4])=[CH:32][CH:31]=2)#[N:34]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 5

HCID 79724-MethylmorpholineHCID 8028TetrahydrofuranHCID 62365Isobutyl chloroformateHCID 685352-Butynoic acidHCID 224666446-Amino-4-[(3-methylphenyl)amino]-3-quinolinecarbonitrile

생성물 1

HCID 19598407N-{3-Cyano-[(3-methylphenyl)amino]-6-quinolinyl}-2-butynamide

시약·촉매·용매

1
HCID 962Water용매

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온도
0 °C

실험 절차

Dissolved 597 mg (7.10 mmol) 2-butynoic acid in 25 ml THF under N2 and chilled to 0° C. Added 950 μl (7.30 mmol) isobutyl chloroformate and 780 μl (7.10 mmol) N-methylmorpholine and stirred for 10 minutes. Added dropwise a solution of 778 mg (2.84 mmol 6-amino-4-[(3-methylphenyl)amino]-3-quinolinecarbonitrile, stirred for 15 minutes at 0° C. and then at 25° C. overnight. Stripped solvent and slurried residue with water, drying the gummy solid in vacuo briefly. Boiled solid in ethyl acetate and collected. Recrystallized from DMF, using ethanol to crash out the product, and dried in vacuo, giving 401 mg of yellow-brown solid: mass spectrum (electrospray m/e): M+H=341.2.

후처리

  1. stirringstirred for 15 minutes at 0° C.
  2. customat 25° C.
  3. customovernight
  4. customdrying the gummy solid in vacuo briefly
  5. customBoiled solid in ethyl acetate and collected
  6. customRecrystallized from DMF
  7. customdried in vacuo

출처 및 근거

ORD 기록
ord-f5462a72fd2e4dbfb7e1042a2f819e90
출처 데이터셋
uspto-grants-1999_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06002008

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