Potassium Carbonate → HCID 66857697, 화합물

HRID 2037542노트

반응식

HRID 2037542 반응식
CS(O[CH2:6][CH2:7][C@@:8]1([C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=2)[O:13][C:12](=[O:14])[N:11]([C@H:15]([C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=3[F:30])=[CH:19][CH:18]=2)[CH3:16])[CH2:10][CH2:9]1)(=O)=O.[NH:38]1[CH:42]=[CH:41][N:40]=[C:39]1[NH2:43].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[NH:38]1[CH:42]=[CH:41][N:40]=[C:39]1[NH:43][CH2:6][CH2:7][C@@:8]1([C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=2)[O:13][C:12](=[O:14])[N:11]([C@H:15]([C:17]2[CH:18]=[CH:19][C:20]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=3[F:30])=[CH:21][CH:22]=2)[CH3:16])[CH2:10][CH2:9]1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 821402-AminoimidazoleHCID 86649947HCID 86649947, 화합물

생성물 1

HCID 66857697HCID 66857697, 화합물수율 19.2%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A mixture of 2-((S)-3-((S)-1-(2′,4′-difluorobiphenyl-4-yl)ethyl)-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-6-yl)ethyl methanesulfonate (40 mg, 0.07 mmol), 1H-imidazol-2-amine (18 mg, 0.21 mmol), K2CO3 (29 mg, 0.21 mmol) in acetonitrile (4 mL) was heated to reflux overnight. The solvent was removed and the residue was partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc and the combined organic layer was washed with brine, dried over Na2SO4, filtered and concentrated to give the crude product. It was purified by preparative HPLC to give (R)-6-(2-(1H-imidazol-2-ylamino)ethyl)-3-((S)-1-(2′,4′-difluorobiphenyl-4-yl)ethyl)-6-(4-fluorophenyl)-1,3-oxazinan-2-one (7 mg, 17%). LC-MS Method 3 tR=1.15, min, m/z=521; 1H NMR (CDCl3): 1.55 (m, 3H), 2.16-2.33 (m, 7H), 2.94 (m, 1H), 3.56 (m, 1H), 4.02 (m, 1H), 5.66 (m, 1H), 6.25 (m, 1H), 6.52 (m, 1H), 6.90 (m, 2H), 7.04 (m, 4H), 7.18 (m, 2H), 7.26 (m, 3H).

후처리

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. customThe solvent was removed
  4. customthe residue was partitioned between EtOAc and water
  5. extractionThe aqueous layer was extracted with EtOAc
  6. washthe combined organic layer was washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give the crude product
  11. customIt was purified by preparative HPLC

출처 및 근거

ORD 기록
ord-e4e4a268dae14959967c9da889e167b4
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08575156B2

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