5-Bromo-2-(trifluoromethyl)pyrimidine → HCID 86690350, 화합물

HRID 2409925노트

반응식

HRID 2409925 반응식
[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

참가 물질

4

반응물 2

HCID 336979635-Bromo-2-(trifluoromethyl)pyrimidineHCID 71233145HCID 71233145, 화합물

생성물 1

HCID 86690350HCID 86690350, 화합물수율 44.3%

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

반응 조건

온도
100 °C

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-6cd57cdc9f4c44a49bd0de4617de9c91
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08815909B2

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