Vertellus → 4-Pyrimidinebutanol,2-amino-6-[[3-fluoro-4-(1h-pyrrolo[2,3-b]pyridin-4-yloxy)phenyl]amino]-

HRID 16462

반응식

HRID 16462 반응식
[NH2:1][C:2]1[N:7]=[C:6]([CH2:8][CH2:9][CH2:10][C:11](OCC)=[O:12])[CH:5]=[C:4]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]3[CH:29]=[CH:28][N:27]=[C:26]4[NH:30][CH:31]=[CH:32][C:25]=34)=[C:19]([F:33])[CH:18]=2)[N:3]=1.[B-].[Na+]>C(O)C>[NH2:1][C:2]1[N:7]=[C:6]([CH2:8][CH2:9][CH2:10][CH2:11][OH:12])[CH:5]=[C:4]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]3[CH:29]=[CH:28][N:27]=[C:26]4[NH:30][CH:31]=[CH:32][C:25]=34)=[C:19]([F:33])[CH:18]=2)[N:3]=1

참가 물질

4

반응물 2

HCID 22959485VertellusHCID 587333944-Pyrimidinebutanoic acid,2-amino-6-[[3-fluoro-4-(1h-pyrrolo[2,3-b]pyridin-4-yloxy)phenyl]amino]-,ethyl ester

생성물 1

HCID 179792724-Pyrimidinebutanol,2-amino-6-[[3-fluoro-4-(1h-pyrrolo[2,3-b]pyridin-4-yloxy)phenyl]amino]-

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

300 mg (0.67 mmol) of 4-(2-amino-6-{[3-fluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)phenyl]amino}pyrimidin-4-yl)butan-1-ol (from example 132) are suspended in 15 ml of ethanol, and 253 mg (6.66 mmol) of sodium borohydrate are added a little at a time at RT. The mixture is stirred at RT for 24 hours and then concentrated, and ethyl acetate and water are added. The organic phase is dried over sodium sulfate. The product is purified by column chromatography (silica gel 60; gradient column, mobile phase: DCM:methanol=9:1 to 3:1). 133 mg (27%) of the starting material are recovered. The product fraction is re-purified by preparative HPLC. This gives the title compound.

후처리

  1. concentrationconcentrated
  2. additionethyl acetate and water are added
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. customThe product is purified by column chromatography (silica gel 60; gradient column, mobile phase: DCM:methanol=9:1 to 3:1)
  5. custom133 mg (27%) of the starting material are recovered
  6. customThe product fraction is re-purified by preparative HPLC

출처 및 근거

ORD 기록
ord-9bdc979f3ea34dbe87830441684289c4
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737153B2

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