Water → HCID 71554405, 화합물

HRID 1776439노트

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HRID 1776439 반응식
[CH2:1]([O:3][C:4]1[CH:32]=[C:31]([F:33])[C:7]([CH2:8][N:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([C:18]3[N:23]=[C:22]([NH:24][C:25]4[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=4)[CH:21]=[CH:20][N:19]=3)=[N:10]2)=[C:6]([F:34])[CH:5]=1)[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:42]([F:47])([F:46])C([O-])=O.[Na+].O>CN(C)C=O.ClCCl.C(O)(C)C>[F:46][CH:42]([F:47])[N:24]([C:25]1[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=1)[C:22]1[CH:21]=[CH:20][N:19]=[C:18]([C:11]2[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:9]([CH2:8][C:7]3[C:31]([F:33])=[CH:32][C:4]([O:3][CH2:1][CH3:2])=[CH:5][C:6]=3[F:34])[N:10]=2)[N:23]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 10796Cesium carbonateHCID 2734985Sodium chlorodifluoroacetateHCID 867324342-[1-(4-ethoxy-2,6-difluorobenzyl)-1H-indazol-3-yl]-N-(pyridin-4-yl)pyrimidin-4-amine

생성물 1

HCID 71554405HCID 71554405, 화합물

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 21966342Isopropanol methylene chloride용매

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온도
100 °C

실험 절차

119.176 mg of 2-[1-(4-ethoxy-2,6-difluorobenzyl)-1H-indazol-3-yl]-N-(pyridin-4-yl)pyrimidin-4-amine (5-1, 0.260 mmol, 1. eq.) were dissolved in 2 ml of dry N,N-dimethylformamide. 254.09 mg of cesium carbonate and 39.63 mg of sodium chloro(difluoro)acetate were added and stirred for two hours at 100° C. bath temperature under nitrogen atmosphere. Then the mixture was portioned between water and dichloromethane/isopropanol 4:1. The phases were separated and the aqueous layer (slightly brown) was extracted twice with dichloromethane/isopropanol 4:1. The combined organic layers were washed with brine, dried over a silicone filter and concentrated in vacuo. The residue was purified by flash chromatography to yield 9 mg (0.02 mmol, 6.13%) of the analytically pure target compound.

후처리

  1. customThe phases were separated
  2. extractionthe aqueous layer (slightly brown) was extracted twice with dichloromethane/isopropanol 4:1
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over a silicone
  5. filtrationfilter
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography
  8. customto yield 9 mg (0.02 mmol, 6.13%) of the analytically pure target compound

출처 및 근거

ORD 기록
ord-d823e8b1fcb445b2bcf03c80f178db60
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09265763B2

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