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Ammonia → [4-(5-Amino-3-methyl-pyridin-2-yl)-piperazin-1-yl]-(2,6-difluoro-phenyl)-methanone

HRID 1993655
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HRID 1993655 반응식
[O-]S(S([O-])=O)=O.[Na+].[Na+].N.[F:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:12]=1[C:18]([N:20]1[CH2:25][CH2:24][N:23]([C:26]2[C:31]([CH3:32])=[CH:30][C:29]([N+:33]([O-])=O)=[CH:28][N:27]=2)[CH2:22][CH2:21]1)=[O:19]>C1COCC1.O>[NH2:33][C:29]1[CH:30]=[C:31]([CH3:32])[C:26]([N:23]2[CH2:22][CH2:21][N:20]([C:18]([C:12]3[C:13]([F:17])=[CH:14][CH:15]=[CH:16][C:11]=3[F:10])=[O:19])[CH2:25][CH2:24]2)=[N:27][CH:28]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 222AmmoniaHCID 24489Sodium DithioniteHCID 68540471(2,6-Difluoro-phenyl)-[4-(3-methyl-5-nitro-pyridin-2-yl)-piperazin-1-yl]-methanone

생성물 1

HCID 68540113[4-(5-Amino-3-methyl-pyridin-2-yl)-piperazin-1-yl]-(2,6-difluoro-phenyl)-methanone수율 44%

시약·촉매·용매 1

HCID 21881883Oxolane--water (1/1)용매

실험 절차

Add Na2S2O4 (10 equiv.) and aqueous ammonia (3 mL/mmol, 32%) to a solution of (2,6-difluoro-phenyl)-[4-(3-methyl-5-nitro-pyridin-2-yl)-piperazin-1-yl]-methanone (3 g, 8.29 mmol) in THF/H2O (166 mL, 1:1). Stir for 30 min., then separate layers. Extract the aqueous layer with DCM, EtOAc and isopropyl alcohol/EtOAc. Combine organic layers and dry over Na2SO4, filter and remove solvent under reduced pressure. Subject crude to a Varian™ SCX column and wash the column with MeOH and then flush off the product with 2 M NH3 in MeOH to obtain 1.2 g of [4-(5-amino-3-methyl-pyridin-2-yl)-piperazin-1-yl]-(2,6-difluoro-phenyl)-methanone (44% yield). ES+(m/z): 333 [M+1]

후처리

  1. extractionExtract the aqueous layer with DCM, EtOAc and isopropyl alcohol/EtOAc
  2. dry with materialCombine organic layers and dry over Na2SO4
  3. filtrationfilter
  4. customremove solvent under reduced pressure
  5. washwash the column with MeOH
  6. customflush off the product with 2 M NH3 in MeOH

출처 및 근거

ORD 기록
ord-320f788b0a6e4e41a97ac5392760f6d4
출처 데이터셋
uspto-grants-2010_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07652015B2

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