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Dimethylamine → 7-(2-Dimethylaminoethoxy)-4-(1H-indazol-6-ylamino)-6-methoxyquinoline-3-carbonitrile

HRID 1595812
노트
인쇄 미리보기

반응식

HRID 1595812 반응식
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([NH:17][C:18]3[CH:26]=[C:25]4[C:21]([CH:22]=[N:23][NH:24]4)=[CH:20][CH:19]=3)=[C:10]([C:15]#[N:16])[CH:11]=[N:12]2)=[CH:7][C:6]=1[O:27][CH3:28].[I-].[Na+].[CH3:31][NH:32][CH3:33]>O1CCCC1.C(OCC)(=O)C>[CH3:31][N:32]([CH3:33])[CH2:2][CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([NH:17][C:18]3[CH:26]=[C:25]4[C:21]([CH:22]=[N:23][NH:24]4)=[CH:20][CH:19]=3)=[C:10]([C:15]#[N:16])[CH:11]=[N:12]2)=[CH:7][C:6]=1[O:27][CH3:28]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 674DimethylamineHCID 5238Sodium IodideHCID 102940037-(2-Chloroethoxy)-4-(1H-indazol-6-ylamino)-6-methoxyquinoline-3-carbonitrile

생성물 1

HCID 102227547-(2-Dimethylaminoethoxy)-4-(1H-indazol-6-ylamino)-6-methoxyquinoline-3-carbonitrile수율 46%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매
HCID 8857
Ethyl Acetate
용매

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온도
135 °C

실험 절차

A mixture of 0.67 g (1 equivalent) of 7-(2-chloroethoxy)-4-(1H-indazol-6-ylamino)-6-methoxyquinoline-3-carbonitrile, 0.097 g (0.4 equivalent) of sodium iodide and 15 ml of 2M dimethylamine in tetrahydrofuran was heated at 135° C. for 14 hours in a sealed tube. The reaction mixture was diluted with ethyl acetate, washed with saturated sodium bicarbonate, the organic layer was dried over magnesium sulfate and concentrated to give 0.50 g. The crude product was purified by chromatography (Silica Gel: ethyl acetate, ethyl acetate/methyl alcohol/triethylamine 6:4:0.1) to give 0.312 g (46%) of pure product. MP 218-219° C. mass spectrum (electrospray m/e): M+H=402.9.

후처리

  1. washwashed with saturated sodium bicarbonate
  2. dry with materialthe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated
  4. customto give 0.50 g
  5. customThe crude product was purified by chromatography (Silica Gel: ethyl acetate, ethyl acetate/methyl alcohol/triethylamine 6:4:0.1)

출처 및 근거

ORD 기록
ord-ab92ef19be8d40558e566399f01c052d
출처 데이터셋
uspto-grants-2001_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06288082B1

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