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Acetyl chloride → N-[6-aminopyrid-3-yl]-5-fluoro-1-[(3-fluorophenyl)methyl]-1H-indole-2-carboxamide

HRID 1943989
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HRID 1943989 반응식
C([NH:4][C:5]1[N:10]=[CH:9][C:8]([NH:11][C:12]([C:14]2[N:15]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=3)[C:16]3[C:21]([CH:22]=2)=[CH:20][C:19]([F:23])=[CH:18][CH:17]=3)=[O:13])=[CH:7][CH:6]=1)(=O)C.C(Cl)(=O)C>CO.C([O-])(O)=O.[Na+].C(OCC)(=O)C>[NH2:4][C:5]1[N:10]=[CH:9][C:8]([NH:11][C:12]([C:14]2[N:15]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=3)[C:16]3[C:21]([CH:22]=2)=[CH:20][C:19]([F:23])=[CH:18][CH:17]=3)=[O:13])=[CH:7][CH:6]=1
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참가 물질

6

반응물 2

HCID 6367Acetyl chlorideHCID 66863369N-[6-(Acetylamino)pyridin-3-yl]-5-fluoro-1-(3-fluorobenzyl)-1H-indole-2-carboxamide

생성물 1

HCID 66863527N-[6-aminopyrid-3-yl]-5-fluoro-1-[(3-fluorophenyl)methyl]-1H-indole-2-carboxamide수율 85%

시약·촉매·용매 3

HCID 887Methanol용매HCID 8857Ethyl Acetate용매
HCID 516892
Sodium Bicarbonate
용매

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온도
0 °C

실험 절차

To a suspension of 0.6 g (1.43 mmol) of N-[6-(acetylamino)pyrid-3-yl]-5-fluoro-1-[(3-fluorophenyl)methyl]-1H-indole-2-carboxamide, prepared according to the protocol described in step 4.1, in 9 mL of anhydrous methanol, stirred at 0° C. under an inert atmosphere, are added dropwise 2.03 mL (28.54 mmol) of acetyl chloride. The reaction mixture is stirred at 0° C. for 30 minutes and then gradually brought to 70° C. and stirred for 48 hours. The reaction mixture is concentrated to dryness. The residue obtained is taken up in a mixture of 200 mL of saturated aqueous NaHCO3 solution and 200 mL of ethyl acetate. The phases are separated by settling and the aqueous phase is extracted with 200 mL of ethyl acetate. The combined organic phases are dried over sodium sulfate and then concentrated under reduced pressure. 0.46 g of the expected product is thus obtained.

후처리

  1. customprepared
  2. stirringThe reaction mixture is stirred at 0° C. for 30 minutes
  3. customgradually brought to 70° C.
  4. stirringstirred for 48 hours
  5. concentrationThe reaction mixture is concentrated to dryness
  6. customThe residue obtained
  7. customThe phases are separated
  8. extractionthe aqueous phase is extracted with 200 mL of ethyl acetate
  9. dry with materialThe combined organic phases are dried over sodium sulfate
  10. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-e1a1f2a2b95d4651ad20d0fa440de22d
출처 데이터셋
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08394820B2

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