Cesium carbonate → N-((1S,2R)-1-(3,5-difluorobenzyl)-2-hydroxy-3-{[1-(3'-methoxy-1,1'-biphenyl-3-yl)cyclopropyl]amino}propyl)acetamide

HRID 14274노트

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HRID 14274 반응식
Br[C:2]1[CH:3]=[C:4]([C:8]2([NH:11][CH2:12][C@@H:13]([OH:28])[C@@H:14]([NH:24][C:25](=[O:27])[CH3:26])[CH2:15][C:16]3[CH:21]=[C:20]([F:22])[CH:19]=[C:18]([F:23])[CH:17]=3)[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[CH3:29][O:30][C:31]1[CH:32]=[C:33](B(O)O)[CH:34]=[CH:35][CH:36]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:23][C:18]1[CH:17]=[C:16]([CH:21]=[C:20]([F:22])[CH:19]=1)[CH2:15][C@H:14]([NH:24][C:25](=[O:27])[CH3:26])[C@H:13]([OH:28])[CH2:12][NH:11][C:8]1([C:4]2[CH:3]=[C:2]([C:35]3[CH:34]=[CH:33][CH:32]=[C:31]([O:30][CH3:29])[CH:36]=3)[CH:7]=[CH:6][CH:5]=2)[CH2:10][CH2:9]1

참가 물질

7

반응물 3

HCID 10796Cesium carbonateHCID 2734370(3-Methoxyphenyl)boronic acidHCID 10097075N-[(1S,2R)-3-{[1-(3-bromophenyl)cyclopropyl]amino}-1-(3,5-difluorobenzyl)-2-hydroxypropyl]acetamide

생성물 1

HCID 57512163N-((1S,2R)-1-(3,5-difluorobenzyl)-2-hydroxy-3-{[1-(3'-methoxy-1,1'-biphenyl-3-yl)cyclopropyl]amino}propyl)acetamide수율 31.4%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
90 °C

실험 절차

To a solution of N-[(1S,2R)-3-{[1-(3-bromophenyl)cyclopropyl]amino}-1-(3,5-difluorobenzyl)-2-hydroxypropyl]acetamide (0.030 g) in DMF (0.75 mL) was added 3-methoxyphenylboronic acid (0.030 g), Cs2CO3 (0.085 g) and Pd(Ph3P)4. The mixture was heated for 12 h at 90° C. The cooled solution was diluted with EtOAc (15 mL) and washed with brine (10 mL×2). The organic layer was dried over Na2SO4, filtered, and evaporated under reduced pressure. The resulting residue was purified by column chromatography to give 0.010 g of the title compound. ES+ found (M+H+):481.

후처리

  1. washwashed with brine (10 mL×2)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe resulting residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-1dab86d8dc884427a1415b11294b5a0e
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07727997B2

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