Triethylamine → (1R,5S)-3-(5-bromo-4-methylpyrimidin-2-yl)-3-azabicyclo[3.1.0]hexane-2-carboxylic acid

HRID 58120ノート

反応式

HRID 58120 の反応式
[Br:1][C:2]1[C:3]([CH3:9])=[N:4][C:5](Cl)=[N:6][CH:7]=1.[C@@H:10]12[CH2:15][C@@H:14]1[CH2:13][NH:12][CH:11]2[C:16]([OH:18])=[O:17].CCN(CC)CC>CCO>[Br:1][C:2]1[C:3]([CH3:9])=[N:4][C:5]([N:12]2[CH2:13][C@@H:14]3[C@@H:10]([CH2:15]3)[CH:11]2[C:16]([OH:18])=[O:17])=[N:6][CH:7]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 2764585(1R,5S)-3-azabicyclo[3.1.0]hexane-2-carboxylic acidHCID 206007365-Bromo-2-chloro-4-methylpyrimidine

生成物 1

HCID 89794796(1R,5S)-3-(5-bromo-4-methylpyrimidin-2-yl)-3-azabicyclo[3.1.0]hexane-2-carboxylic acid

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
75 °C

実験手順

In a 40 mL vial were mixed 5-bromo-2-chloro-4-methylpyrimidine (438 mg, 2.109 mmol), (1R,5S)-3-azabicyclo[3.1.0]hexane-2-carboxylic acid (295 mg, 2.320 mmol), and Et3N (0.882 mL, 6.33 mmol) in EtOH (90 mL). The resulting yellow solution was stirred at 75° C. for 3 days. The reaction mixture was subsequently partitioned between 1N HCl (40 mL) and EtOAc (40 mL). The phases were separated and the aqueous layer was back-extracted with EtOAc (75 mL). The organic layers were combined, washed with brine (40 mL), dried over Na2SO4, filtered, and concentrated to give the title compound as a white solid, which was used without further purification (660 mg).

後処理

  1. customThe reaction mixture was subsequently partitioned between 1N HCl (40 mL) and EtOAc (40 mL)
  2. customThe phases were separated
  3. extractionthe aqueous layer was back-extracted with EtOAc (75 mL)
  4. washwashed with brine (40 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-f036e74a37cf4e0286b15f3995a815a7
出典データセット
uspto-grants-2016_09
特許番号
US09434743B2

反応ノート

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