Cesium carbonate → HCID 11983634, 화합물

HRID 602698노트

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HRID 602698 반응식
[F:1][C:2]1[CH:3]=[C:4]([C@H:9]([CH:14]2[CH2:17][NH:16][CH2:15]2)[C:10]([F:13])([CH3:12])[CH3:11])[CH:5]=[C:6]([F:8])[CH:7]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH:25]([C:34]1[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=1)[C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=1)[C:29]#[N:30]>C(#N)C>[Cl:40][C:37]1[CH:36]=[CH:35][C:34]([C@H:25]([N:16]2[CH2:15][CH:14]([C@@H:9]([C:4]3[CH:3]=[C:2]([F:1])[CH:7]=[C:6]([F:8])[CH:5]=3)[C:10]([F:13])([CH3:12])[CH3:11])[CH2:17]2)[C:26]2[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=2)[C:29]#[N:30])=[CH:39][CH:38]=1

참가 물질

5

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HCID 10796Cesium carbonateHCID 670553513-[Bromo(4-chlorophenyl)methyl]benzonitrileHCID 670553593-[(1S)-1-(3,5-Difluorophenyl)-2-fluoro-2-methylpropyl]azetidine

생성물 1

HCID 11983634HCID 11983634, 화합물

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
60 °C

실험 절차

A solution of the crude amine from Step 1 and 3.4 g (1.1 mmole) of Cs2CO3 in 10 mL dry acetonitrile was stirred at rt in a flask fitted with a small Dean-Stark trap. After 15 minutes, 2.3 g (7.5 mmole) of 3-[bromo(4-chlorophenyl)methyl]benzonitrile was added and the mixture was heated at 60° C. After 18 h, the solution was filtered through CELITE and the residue was washed with acetonitrile. The combined filtrates were concentrated and the residue was purified by flash chromatography using a step gradient of 5 to 20% ethyl acetate-hexane. Fractions containing the faster product diastereomer were pooled and concentrated to afford the title compound; 1NMR(CDCl3) δ 1.25 (t, J=22 Hz, 6H), 2.33 (t, J=6.5 Hz, 1H), 2.83-2.89 (m, 2H), 3.09-3.11 (m, 2H), 3.60 (m, 1H), 4.24 (s, 1H), 6.68-6.71 (m, 3H), 7.21-7.8 (m, 8H); Mass Spectrum: m/e=469 (M+1, 35Cl) and 471 (M+1, 37Cl).

후처리

  1. customfitted with a small Dean-Stark trap
  2. waitAfter 18 h
  3. filtrationthe solution was filtered through CELITE
  4. washthe residue was washed with acetonitrile
  5. concentrationThe combined filtrates were concentrated
  6. customthe residue was purified by flash chromatography
  7. additionFractions containing the faster product diastereomer
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-ad4314e04f384aacbd51cdc5e50c2d37
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07906503B2

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