Acetyl chloride → HCID 86732448, 화합물

HRID 1776419노트

반응식

HRID 1776419 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(N(CC)CC)C.[C:42](Cl)(=[O:44])[CH3:43]>ClCCl>[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]([N:24]([C:25]4[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=4)[C:42](=[O:44])[CH3:43])[CH:21]=[CH:20][N:19]=3)=[N:10]2)=[C:6]([F:34])[CH:5]=1)[CH3:2]

참가 물질

5

반응물 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 867324342-[1-(4-ethoxy-2,6-difluorobenzyl)-1H-indazol-3-yl]-N-(pyridin-4-yl)pyrimidin-4-amine

생성물 1

HCID 86732448HCID 86732448, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

100 mg of 2-[1-(4-ethoxy-2,6-difluorobenzyl)-1H-indazol-3-yl]-N-(pyridin-4-yl)-pyrimidin-4-amine (5-1-1, 0.218 mmol, 1. eq.) was dissolved in 2 ml of dry dichloromethane. First 94 μl of dry N,N-diethylethanamine (0.676 mmol, 3.1 eq.) and then 23 μl of acetyl chloride (0.327 mmol, 1.5 eq,) were added under nitrogen atmosphere. The reaction mixture was stirred at room temperature for 18 hours. Then the mixture was partitioned between water and dichloromethane. The phases were separated and the aqueous layer was extracted twice with dichloromethane. The combined organic layers were washed with brine, dried over a silicon filter and concentrated in vacuo. The residue was purified by flash chromatography and preparative TLC to yield 29.8 mg (0.06 mmol, 26.8%) of the analytically pure target compound.

후처리

  1. customThen the mixture was partitioned between water and dichloromethane
  2. customThe phases were separated
  3. extractionthe aqueous layer was extracted twice with dichloromethane
  4. washThe combined organic layers were washed with brine
  5. customdried over a silicon
  6. filtrationfilter
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography and preparative TLC
  9. customto yield 29.8 mg (0.06 mmol, 26.8%) of the analytically pure target compound

출처 및 근거

ORD 기록
ord-f8c0663be8474d649b85cb58ed71d329
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09265763B2

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