5-Bromo-2-(trifluoromethyl)pyrimidine → HCID 86690350、化合物

HRID 2409925ノート

反応式

HRID 2409925 の反応式
[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([NH:7][C@@H:8]2[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]2[NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:2]1.Br[C:23]1[CH:24]=[N:25][C:26]([C:29]([F:32])([F:31])[F:30])=[N:27][CH:28]=1>CC(N(C)C)=O>[F:30][C:29]([F:32])([F:31])[C:26]1[N:27]=[CH:28][C:23]([N:1]2[CH2:6][CH2:5][CH2:4][CH:3]([NH:7][C@@H:8]3[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]3[NH:14][C:15](=[O:21])[O:16][C:17]([CH3:18])([CH3:20])[CH3:19])[CH2:2]2)=[CH:24][N:25]=1

参加物

4

反応物 2

HCID 336979635-Bromo-2-(trifluoromethyl)pyrimidineHCID 71233145HCID 71233145、化合物

生成物 1

HCID 86690350HCID 86690350、化合物収率 44.3%

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

反応条件

温度
100 °C

実験手順

Dimethylacetamide (5.25 mL) was added to a round bottom flask containing tert-butyl (1R,2R)-2-(piperidin-3-ylamino)cyclohexylcarbamate (0.47 gm, 1.58 mmol) and 5-bromo-2-(trifluoromethyl)pyrimidine (0.43 gm, 1.89 mmol). The reaction mixture was then heated at 100° C. After 48 h heating was stopped. The reaction mixture was partitioned between EtOAc and sat. NaHCO3. The organic phase was isolated, washed with saturated aqueous NaCl, dried over MgSO4, filtered and concentrated. The resulting residue was purified using silica gel chromatography eluting with a gradient of 0-100% EtOAc/Hexanes holding at 100% EtOAc to give the diastereomeric product, tert-butyl (1R,2R)-2-(1-(2-(trifluoromethyl)pyrimidin-5-yl)piperidin-3-ylamino)cyclohexylcarbamate, (0.31 gm, 0.70 mmol, 44% yield) as light yellow solid. Anal. Calcd. for C21H32F3N5O2 m/z 443.3, found: 444.3 (M+H)+.

後処理

  1. temperatureAfter 48 h heating
  2. customThe reaction mixture was partitioned between EtOAc and sat. NaHCO3
  3. customThe organic phase was isolated
  4. washwashed with saturated aqueous NaCl
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue was purified
  9. washeluting with a gradient of 0-100% EtOAc/Hexanes holding at 100% EtOAc

出典と根拠

ORDレコード
ord-6cd57cdc9f4c44a49bd0de4617de9c91
出典データセット
uspto-grants-2014_08
特許番号
US08815909B2

反応ノート

読み込み中…