Serinol → 2-[[7-Amino-2-[[(2,3-difluorophenyl)methyl]thio]-4-pteridinyl]amino]-1,3-propanediol

HRID 1789938노트

반응식

HRID 1789938 반응식
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][S:10][C:11]1[N:20]=[C:19](SCC2C=CC=C(F)C=2F)[C:18]2[C:13](=[N:14][C:15]([NH2:31])=[CH:16][N:17]=2)[N:12]=1.[NH2:32][CH:33]([CH2:36][OH:37])[CH2:34][OH:35]>CN1C=CN=C1>[NH3:12].[NH2:31][C:15]1[N:14]=[C:13]2[C:18]([C:19]([NH:32][CH:33]([CH2:36][OH:37])[CH2:34][OH:35])=[N:20][C:11]([S:10][CH2:9][C:3]3[CH:4]=[CH:5][CH:6]=[C:7]([F:8])[C:2]=3[F:1])=[N:12]2)=[N:17][CH:16]=1

참가 물질

5

반응물 2

HCID 68294SerinolHCID 220370392,4-Bis[[(2,3-difluorophenyl)methyl]thio]-7-pteridinamine

생성물 2

HCID 222AmmoniaHCID 102719362-[[7-Amino-2-[[(2,3-difluorophenyl)methyl]thio]-4-pteridinyl]amino]-1,3-propanediol수율 39.2%

시약·촉매·용매 1

HCID 13901-Methylimidazole용매

실험 절차

A solution of the product from example 1, step (c) (0.12 g) and serinol (330 mg) in 1-methylimidazole (1 ml) was heated at 130° C. for 90 minutes. After cooling, the reaction mixture was partitioned between ethyl acetate and saturated aqueous ammonium chloride. The organic phase was dried over magnesium sulphate, filtered and evaporated to give a brown solid which was purified by silica gel flash column chromatography, eluting with 200:20:1 dichloromethane:methanol:880 ammonia solution, to give the title compound as a pale brown solid (0.02 g).

후처리

  1. temperatureAfter cooling
  2. customthe reaction mixture was partitioned between ethyl acetate and saturated aqueous ammonium chloride
  3. dry with materialThe organic phase was dried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. customto give a brown solid which
  7. customwas purified by silica gel flash column chromatography
  8. washeluting with 200:20:1 dichloromethane

출처 및 근거

ORD 기록
ord-f99cb156d7224367b03f8c191091bbb7
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07071193B2

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