3,3,3-Trifluoropropanal → HCID 66802376, 화합물

HRID 341456

반응식

HRID 341456 반응식
Cl.[CH3:2][N:3]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:4]1[N:9]=[C:8]([NH2:10])[N:7]=[C:6]([C:11]2[N:15]=[C:14]([C@@H:16]3[CH2:20][CH2:19][CH2:18][NH:17]3)[O:13][N:12]=2)[N:5]=1.C([O-])(=O)C.[Na+].[F:32][C:33]([F:38])([F:37])[CH2:34][CH:35]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(Cl)Cl>[CH3:2][N:3]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:4]1[N:9]=[C:8]([NH2:10])[N:7]=[C:6]([C:11]2[N:15]=[C:14]([C@@H:16]3[CH2:20][CH2:19][CH2:18][N:17]3[CH2:35][CH2:34][C:33]([F:38])([F:37])[F:32])[O:13][N:12]=2)[N:5]=1

참가 물질

7

반응물 4

HCID 680283,3,3-TrifluoropropanalHCID 517045Sodium AcetateHCID 5049666Sodium triacetoxyborohydrideHCID 668025652-N-methyl-2-N-phenyl-6-{5-[(2S)-pyrrolidin-2-yl]-1,2,4-oxadiazol-3-yl}-1,3,5-triazine-2,4-diamine hydrochloride

생성물 1

HCID 66802376HCID 66802376, 화합물수율 19.4%

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 6344Dichloromethane용매

실험 절차

To a solution of 2-N-methyl-2-N-phenyl-6-{5-[(2S)-pyrrolidin-2-yl]-1,2,4-oxadiazol-3-yl}-1,3,5-triazine-2,4-diamine hydrochloride (Example 438, 0.2 g, 0.535 mmol) in DCE (5 mL) was added sodium acetate (0.07 g, 0.8 mmol) and 3,3,3-trifluoropropanal (0.12 g, 1.070 mmol) and the mixture was stirred for 1 h at room temperature. Sodium triacetoxyborohydride (0.17 g, 0.8 mmol) was added and the reaction mixture was stirred for 2 h at room temperature. DCM was added and the mixture was washed with saturated aq. sodium bicarbonate, and then brine. The organic layer was dried over sodium sulfate and concentrated under vacuum. The residue was purified by FCC, eluting with 20-100% EtOAc in heptane to afford the title compound (0.045 g, 19%).

후처리

  1. stirringthe reaction mixture was stirred for 2 h at room temperature
  2. washthe mixture was washed with saturated aq. sodium bicarbonate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by FCC
  6. washeluting with 20-100% EtOAc in heptane

출처 및 근거

ORD 기록
ord-bcb1dbc97c884400b9c95defbcc88bec
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895733B2

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