1,8-Diazabicyclo(5.4.0)undec-7-ene → (S)-N-(5-(3-(hydroxymethyl)-5-(trifluoromethyl)benzyl)-2,3-dihydro-1H-inden-2-yl)methanesulfonamide

HRID 473109ノート

反応式

HRID 473109 の反応式
[NH2:1][C@@H:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:11][C:12]3[CH:13]=[C:14]([CH2:22][OH:23])[CH:15]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:17]=3)[CH:8]=2)[CH2:3]1.[CH3:24][S:25](OC1C(F)=C(F)C(F)=C(F)C=1F)(=[O:27])=[O:26].N1CCCN2CCCCCC=12>C1COCC1>[OH:23][CH2:22][C:14]1[CH:13]=[C:12]([CH:17]=[C:16]([C:18]([F:19])([F:20])[F:21])[CH:15]=1)[CH2:11][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[CH2:3][C@H:2]([NH:1][S:25]([CH3:24])(=[O:27])=[O:26])[CH2:10]2

参加物

5

反応物 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2783233Perfluorophenyl methanesulfonateHCID 66733722(S)-(3-((2-amino-2,3-dihydro-1H-inden-5-yl)methyl)-5-(trifluoromethyl)phenyl)methanol

生成物 1

HCID 70222665(S)-N-(5-(3-(hydroxymethyl)-5-(trifluoromethyl)benzyl)-2,3-dihydro-1H-inden-2-yl)methanesulfonamide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To (S)-(3-((2-amino-2,3-dihydro-1H-inden-5-yl)methyl)-5-(trifluoromethyl)phenyl)methanol (50, mg, 0.16 mmol) in THF (1 mL) was added perfluorophenyl methanesulfonate (39 mg, 0.15 mmol) followed by 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine (34.1 mg 0.22 mmol). The reaction was allowed to stir at RT overnight before removing the solvent in vacuo. The sample was redissolved in DMSO (500 μL) before purifying by reverse phase preparative HPLC-MS to give the title compound as a clear film (11 mg, 17.2%). MS (ESI): m/z [M+H]+ 400.1

後処理

  1. custombefore removing the solvent in vacuo
  2. dissolutionThe sample was redissolved in DMSO (500 μL)
  3. custombefore purifying by reverse phase preparative HPLC-MS

出典と根拠

ORDレコード
ord-96116dae59a445a8b8af620b65340a69
出典データセット
uspto-grants-2014_01
特許番号
US08633237B2

反応ノート

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