Sodium Methoxide → 3-Amino-5-chloro-6-isopropoxy-4-methyl-thieno[2,3-b]pyridine-2-carboxylic acid cyclopropylamide

HRID 656636노트

반응식

HRID 656636 반응식
[CH:1]1([NH:4][C:5](=[O:8])[CH2:6][SH:7])[CH2:3][CH2:2]1.C[O-].[Na+].Cl[C:13]1[N:20]=[C:19]([O:21][CH:22]([CH3:24])[CH3:23])[C:18]([Cl:25])=[C:17]([CH3:26])[C:14]=1[C:15]#[N:16].ClC1C(Cl)=NC(OC(C)C)=C(C=1C)C#N>CO.CCOC(C)=O.CCCCCC.O>[CH:1]1([NH:4][C:5]([C:6]2[S:7][C:13]3=[N:20][C:19]([O:21][CH:22]([CH3:23])[CH3:24])=[C:18]([Cl:25])[C:17]([CH3:26])=[C:14]3[C:15]=2[NH2:16])=[O:8])[CH2:3][CH2:2]1

참가 물질

9

반응물 4

HCID 10942334Sodium MethoxideHCID 55207200N-cyclopropyl-2-mercaptoacetamideHCID 862419142,5-Dichloro-6-isopropoxy-4-methyl-nicotinonitrileHCID 862419165,6-Dichloro-2-isopropoxy-4-methyl-nicotinonitrile

생성물 1

HCID 115518363-Amino-5-chloro-6-isopropoxy-4-methyl-thieno[2,3-b]pyridine-2-carboxylic acid cyclopropylamide

시약·촉매·용매 4

HCID 887Methanol용매HCID 962Water용매HCID 8058Hexane용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of N-cyclopropyl-2-mercapto-acetamide (0.498 g, 3.80 mmol) in MeOH (5 ml) is added sodium methoxide solution (25% wt. in MeOH)(0.652 ml, 2.85 mmol). The resulting solution is stirred at room temperature for 30 minutes, then treated with a 1:1 mixture of 2,5-dichloro-6-isopropoxy-4-methyl-nicotinonitrile and 5,6-dichloro-2-isopropoxy-4-methyl-nicotinonitrile (0.400 g, 1.63 mmol). The reaction vessel is sealed, heated at 100° C. for 2.5 hours, and cooled to room temperature. The reaction mixture is poured over water (60 ml), then extracted with EtOAc (2×40 ml). The combined organic layers are washed with brine (50 ml), dried (anhydrous magnesium sulfate), filtered, and concentrated to give a yellow-brown solid. Flash chromatography (1.5:1 hexane:EtOAc) affords the title compound as a tan solid (20 mg). Mass (m/z): 340.1 (M++1).

후처리

  1. customThe reaction vessel is sealed
  2. temperatureheated at 100° C. for 2.5 hours
  3. temperaturecooled to room temperature
  4. extractionextracted with EtOAc (2×40 ml)
  5. washThe combined organic layers are washed with brine (50 ml)
  6. dry with materialdried (anhydrous magnesium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a yellow-brown solid

출처 및 근거

ORD 기록
ord-49a6f6e6a12047608104458db7a9990b
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08071776B2

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