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Epichlorohydrin → HCID 86749231, 화합물

HRID 1586157
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HRID 1586157 반응식
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15]([NH:16][CH2:17][CH:18]4[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]4)=[C:6]2[CH:5]=[N:4]1)=[CH:13][C:12]([OH:24])=[CH:11][CH:10]=3)[CH3:2].[OH-].[K+].[CH2:27]([CH:29]1[O:31][CH2:30]1)Cl>CS(C)=O>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15]([NH:16][CH2:17][CH:18]4[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]4)=[C:6]2[CH:5]=[N:4]1)=[CH:13][C:12]([O:24][CH2:27][CH:29]1[O:31][CH2:30]1)=[CH:11][CH:10]=3)[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 7835EpichlorohydrinHCID 14797Potassium HydroxideHCID 9818690HCID 9818690, 화합물

생성물 1

HCID 86749231HCID 86749231, 화합물

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

A mixture of 1-ethyl-6-hydroxy-N-(cyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine (2 g), DMSO (30 ml) and KOH (2 g) is stirred at room temperature for 0.5 hours, then epichlorohydrin (0.49 ml) is added, and the mixture is stirred overnight. The reaction mixture is partitioned between CH2Cl2 and water, and then the CH2Cl2 layer is separated and evaporated. The residue is purified by column chromatography on silica gel eluting with ethyl acetate to afford the product that is combined with the product from a similar experimental. The combined material is purified further by column chromatography on silica gel eluting with 90% ether/t-butylmethylether, followed by crystallization from ether, to afford 1-ethyl-6-(2,3-epoxypropoxy)-N-(cyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4amine, m.p. 168°-170° C.

후처리

  1. stirringthe mixture is stirred overnight
  2. customThe reaction mixture is partitioned between CH2Cl2 and water
  3. customthe CH2Cl2 layer is separated
  4. customevaporated
  5. customThe residue is purified by column chromatography on silica gel eluting with ethyl acetate
  6. customto afford the product that
  7. customThe combined material is purified further by column chromatography on silica gel eluting with 90% ether/t-butylmethylether
  8. customfollowed by crystallization from ether

출처 및 근거

ORD 기록
ord-78f48aeba1f64a0d8f6225441461db1b
출처 데이터셋
uspto-grants-1999_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05942520

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