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1-Bromo-2-Chloroethane → 3-[3-[[1-[2-(2-chloroethoxy)phenyl]cyclopropyl]amino]-2-oxo-1(2H)-pyrazinyl]-N-cyclopropyl-5-fluoro-4-methyl-benzamide

HRID 337093
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HRID 337093 반응식
[CH:1]1([NH:4][C:5](=[O:32])[C:6]2[CH:11]=[C:10]([N:12]3[CH:17]=[CH:16][N:15]=[C:14]([NH:18][C:19]4([C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=5[OH:28])[CH2:21][CH2:20]4)[C:13]3=[O:29])[C:9]([CH3:30])=[C:8]([F:31])[CH:7]=2)[CH2:3][CH2:2]1.Br[CH2:34][CH2:35][Cl:36].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[Cl:36][CH2:35][CH2:34][O:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[C:19]1([NH:18][C:14]2[C:13](=[O:29])[N:12]([C:10]3[CH:11]=[C:6]([CH:7]=[C:8]([F:31])[C:9]=3[CH3:30])[C:5]([NH:4][CH:1]3[CH2:2][CH2:3]3)=[O:32])[CH:17]=[CH:16][N:15]=2)[CH2:21][CH2:20]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 78491-Bromo-2-ChloroethaneHCID 10796Cesium carbonateHCID 66690808N-Cyclopropyl-3-fluoro-5-[3-[[1-(2-hydroxyphenyl)cyclopropyl]amino]-2-oxo-1(2H)-pyrazinyl]-4-methyl-benzamide2회

생성물 1

HCID 666898043-[3-[[1-[2-(2-chloroethoxy)phenyl]cyclopropyl]amino]-2-oxo-1(2H)-pyrazinyl]-N-cyclopropyl-5-fluoro-4-methyl-benzamide

시약·촉매·용매 1

HCID 6342
Acetonitrile
용매

실험 절차

N-Cyclopropyl-3-fluoro-5-[3-[[1-(2-hydroxyphenyl)cyclopropyl]amino]-2-oxo-1(2H)-pyrazinyl]-4-methyl-benzamide (Example 259c 5 g), 1-bromo-2-chloroethane (9.58 mL) and cesium carbonate (37.5 g) were stirred together in acetonitrile (200 mL) at 80° C. under nitrogen for 16 h. The cooled reaction mixture was evaporated to dryness, diluted with water (500 mL) and extracted with dichloromethane (3×300 mL). The combined organics were dried (MgSO4), filtered and evaporated. The residue was triturated with 1:1 iso-hexane:diethyl ether to give the subtitle compound (4.60 g).

후처리

  1. customThe cooled reaction mixture
  2. customwas evaporated to dryness
  3. additiondiluted with water (500 mL)
  4. extractionextracted with dichloromethane (3×300 mL)
  5. dry with materialThe combined organics were dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was triturated with 1:1 iso-hexane

출처 및 근거

ORD 기록
ord-0b096abe8b094f8497e96e6c1da18871
출처 데이터셋
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08889692B2

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