Diisopropylethylamine → ((2S,3R)-2-(((5-Fluoropyrimidin-2-yl)amino)methyl)-3-methylpiperidin-1-yl)(5-methyl-2-(1H-pyrazol-1-yl)phenyl)methanone

HRID 61099

反応式

HRID 61099 の反応式
[NH2:1][CH2:2][C@@H:3]1[C@H:8]([CH3:9])[CH2:7][CH2:6][CH2:5][N:4]1[C:10]([C:12]1[CH:17]=[C:16]([CH3:18])[CH:15]=[CH:14][C:13]=1[N:19]1[CH:23]=[CH:22][CH:21]=[N:20]1)=[O:11].Cl[C:25]1[N:30]=[CH:29][C:28]([F:31])=[CH:27][N:26]=1.CCN(C(C)C)C(C)C>CC#N>[F:31][C:28]1[CH:27]=[N:26][C:25]([NH:1][CH2:2][C@@H:3]2[C@H:8]([CH3:9])[CH2:7][CH2:6][CH2:5][N:4]2[C:10]([C:12]2[CH:17]=[C:16]([CH3:18])[CH:15]=[CH:14][C:13]=2[N:19]2[CH:23]=[CH:22][CH:21]=[N:20]2)=[O:11])=[N:30][CH:29]=1

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 5834662-Chloro-5-fluoropyrimidineHCID 117727705((2S,3R)-2-(Aminomethyl)-3-methylpiperidin-1-yl)(5-methyl-2-(1H-pyrazol-1-yl)phenyl)methanone

生成物 1

HCID 117728267((2S,3R)-2-(((5-Fluoropyrimidin-2-yl)amino)methyl)-3-methylpiperidin-1-yl)(5-methyl-2-(1H-pyrazol-1-yl)phenyl)methanone

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
100 °C

実験手順

A mixture of ((2S,3R)-2-(aminomethyl)-3-methylpiperidin-1-yl)(5-methyl-2-(1H-pyrazol-1-yl)phenyl)methanone (30 mg, 96 μmol), 2-chloro-5-fluoropyrimidine (18 μl, 144 μmol) and anhydrous DIPEA (50 g, 288 μmol) in CH3CN (2 mL) was heated at 100° C. for 3 days. The mixture was cooled to rt and the solvent was removed in vacuo. The crude was dissolved in EtOAc and washed with satd. aq. NaHCO3, brine, and dried (MgSO4). The solvent was removed and the crude was purified by reverse-phase preparative HPLC to afford the title compound. MS (ESI) 409 (M+H).

後処理

  1. temperatureThe mixture was cooled to rt
  2. customthe solvent was removed in vacuo
  3. dissolutionThe crude was dissolved in EtOAc
  4. washwashed with satd
  5. dry with materialaq. NaHCO3, brine, and dried (MgSO4)
  6. customThe solvent was removed
  7. customthe crude was purified by reverse-phase preparative HPLC

出典と根拠

ORDレコード
ord-4fc5c6f4fe5845b2bff165dfb592b984
出典データセット
uspto-grants-2016_09
特許番号
US09440982B2

関連ノート

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