1,1,1-Trimethoxy-2-chloroethane → 2-Chloromethyl-1-ethyl-6-(3-trifluoromethyl-phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile

HRID 2246457노트

반응식

HRID 2246457 반응식
[O-]S(C(F)(F)F)(=O)=O.[Yb+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O.[Cl:26][CH2:27][C:28](OC)(OC)OC.[NH2:35][C:36]1[C:37]([C:55]#[N:56])=[N:38][C:39]([C:45]2[CH:50]=[CH:49][CH:48]=[C:47]([C:51]([F:54])([F:53])[F:52])[CH:46]=2)=[CH:40][C:41]=1[NH:42][CH2:43][CH3:44]>C(#N)C>[Cl:26][CH2:27][C:28]1[N:42]([CH2:43][CH3:44])[C:41]2[CH:40]=[C:39]([C:45]3[CH:50]=[CH:49][CH:48]=[C:47]([C:51]([F:54])([F:52])[F:53])[CH:46]=3)[N:38]=[C:37]([C:55]#[N:56])[C:36]=2[N:35]=1

참가 물질

5

반응물 3

HCID 1447021,1,1-Trimethoxy-2-chloroethaneHCID 2733225Ytterbium triflateHCID 685171643-Amino-4-ethylamino-6-(3-trifluoromethylphenyl)-pyridine-2-carbonitrile

생성물 1

HCID 685169312-Chloromethyl-1-ethyl-6-(3-trifluoromethyl-phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile수율 87%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

Ytterbium triflate (1.16 g, 1.8 mmol) and 2-chloro-1,1,1-trimethoxyethane (7.56 mL, 56.0 mmol) was added to a solution of 3-amino-4-ethylamino-6-(3-trifluoromethylphenyl)-pyridine-2-carbonitrile (5.73 g, 18.7 mmol) in acetonitrile (150 mL). The mixture was refluxed for 48 hours, then concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was triturated with diethyl ether, filtered off to afford the title compound (5.92 g, 87%) as a solid. 1H NMR (DMSO-d6) δ: 8.85 (s, 1H); 8.50-8.00 (m, 2H); 7.90-7.70 (m, 2H); 5.26 (s, 2H); 4,55-4.45 (m, 2H); 1.48 (t, J=7 Hz, 3H). MS m/z: 365 (M+1).

후처리

  1. temperatureThe mixture was refluxed for 48 hours
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was partitioned between ethyl acetate and water
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was triturated with diethyl ether
  8. filtrationfiltered off

출처 및 근거

ORD 기록
ord-b7415f9f57fc40bdad8908c685e69f13
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07687515B2

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