Triethylamine → HCID 66988891, 화합물

HRID 2097679노트

반응식

HRID 2097679 반응식
[NH:1]1[CH:10]2[CH:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.Cl[C:19](Cl)([O:21]C(=O)OC(Cl)(Cl)Cl)Cl.CN(C1C=CC=CN=1)C.[O:39]([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=1[C:52]1[N:53]=[N:54][NH:55][C:56]=1[C:57]([NH:59][C@@H:60]1[CH2:65][C@H:64]2[CH2:66][C@@H:62]([C:63]2([CH3:68])[CH3:67])[C@H:61]1[CH3:69])=[O:58])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>ClCCl.C(OCC)(=O)C.[Cl-].[Na+].O>[N:1]1([C:19]([N:55]2[C:56]([C:57]([NH:59][C@@H:60]3[CH2:65][C@H:64]4[CH2:66][C@@H:62]([C:63]4([CH3:68])[CH3:67])[C@H:61]3[CH3:69])=[O:58])=[C:52]([C:47]3[CH:48]=[CH:49][CH:50]=[CH:51][C:46]=3[O:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[N:53]=[N:54]2)=[O:21])[CH:10]2[CH:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3][CH2:2]1

참가 물질

9

반응물 5

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 92911DecahydroquinolineHCID 94429TriphosgeneHCID 178461482HCID 178461482, 화합물

생성물 1

HCID 66988891HCID 66988891, 화합물

시약·촉매·용매 3

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매HCID 57417360Sodium chloride; water용매

실험 절차

To a solution of decahydroquinoline (10) (1.5 equiv) in dry dichloromethane (0.5 M) under argon was added triethylamine (1.5 equiv) followed by triphosgene (1.5 equiv). The resulting heterogeneous mixture was stirred at room temperature for 15 minutes, concentrated in vacuum and the residue was taken up in 1:1 dry toluene/THF (0.25 M with respect to amine), and treated with dimethylaminopyridine (DMAP) (1.0 equiv) and triazole (13) (1.0 equiv). The resulting mixture was heated to reflux for 1.5 hours, cooled to room temperature and diluted with ethyl acetate and brine, and the aqueous and organic layers were separated. The organic layer was washed with brine, 10% aqueous HCl, then brine, and dried over MgSO4, filtered and concentrated in vacuo. The residue is purified by flash chromatography on silica gel (ethyl acetate/hexanes) to provide 1-(decahydroquinoline-1-carbonyl)-4-(2-phenoxyphenyl)-N-((1R,2R,3R,5R)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl)-1H-1,2,3-triazole-5-carboxamide (14) which was further purified by preparative HPLC (1% formic acid) to afford a lyophilized powder.

후처리

  1. concentrationconcentrated in vacuum
  2. temperatureThe resulting mixture was heated
  3. temperatureto reflux for 1.5 hours
  4. temperaturecooled to room temperature
  5. customthe aqueous and organic layers were separated
  6. washThe organic layer was washed with brine, 10% aqueous HCl
  7. dry with materialbrine, and dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue is purified by flash chromatography on silica gel (ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-38d3b1e4955d40f792a35de2cda75cb0
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08450350B2

반응 노트

불러오는 중…