Triethylamine → 6-{3-Chloro-4-[2-(4-cyano-3,5-dimethyl-phenyl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-phenoxy}-4-trifluoromethyl-nicotinic acid methyl ester

HRID 2096854노트

반응식

HRID 2096854 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[CH:9]([CH3:26])[C:10]([C:16]1[CH:23]=[C:22]([CH3:24])[C:19]([C:20]#[N:21])=[C:18]([CH3:25])[CH:17]=1)([OH:15])[C:11]([F:14])([F:13])[F:12].[CH3:27][O:28][C:29](=[O:41])[C:30]1[C:35]([C:36]([F:39])([F:38])[F:37])=[CH:34][C:33](Cl)=[N:32][CH:31]=1.C(N(CC)CC)C.N12CCN(CC1)CC2>CN(C)C(=O)C.CCOC(C)=O.O>[CH3:27][O:28][C:29](=[O:41])[C:30]1[C:35]([C:36]([F:37])([F:38])[F:39])=[CH:34][C:33]([O:8][C:6]2[CH:5]=[CH:4][C:3]([CH:9]([CH3:26])[C:10]([C:16]3[CH:17]=[C:18]([CH3:25])[C:19]([C:20]#[N:21])=[C:22]([CH3:24])[CH:23]=3)([OH:15])[C:11]([F:14])([F:12])[F:13])=[C:2]([Cl:1])[CH:7]=2)=[N:32][CH:31]=1

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 9237DabcoHCID 2775340Methyl 6-chloro-4-(trifluoromethyl)nicotinateHCID 666970264-[2-(2-Chloro-4-hydroxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-2,6-dimethyl-benzonitrile

생성물 1

HCID 723101226-{3-Chloro-4-[2-(4-cyano-3,5-dimethyl-phenyl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-phenoxy}-4-trifluoromethyl-nicotinic acid methyl ester수율 86.3%

시약·촉매·용매 3

HCID 962Water용매HCID 8857Ethyl Acetate용매HCID 31374Dimethylacetamide용매

실험 절차

To a solution of 4-[2-(2-chloro-4-hydroxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-2,6-dimethyl-benzonitrile (Example 141, step 5, 100 mg) in N,N-dimethylacetamide (1 ml) were added methyl-6-chloro-4-(trifluoromethyl)-nicotinate (75 mg), triethylamine (34 mg) and 1,4-diazabicyclo[2.2.2]octane (4 mg). The mixture was stirred at room temperature for 6 h and then diluted with EtOAc. Water was added. The mixture was extracted with EtOAc. The organic phase was washed with water, dried (MgSO4), filtered and concentrated. The product was purified by chromatography (SiO2, cyclohexane/EtOAc 1:0=>2:3) to give the title compound (132 mg) as a colorless solid. MS (m/e, ISP neg. ion)=585.1 [M−H+].

후처리

  1. extractionThe mixture was extracted with EtOAc
  2. washThe organic phase was washed with water
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe product was purified by chromatography (SiO2, cyclohexane/EtOAc 1:0=>2:3)

출처 및 근거

ORD 기록
ord-5f7f3af30d0d45b3a3234b3bd58fbbf3
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08450313B2

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