Alpha-chlorobenzaldoxime → 5-(4-(Isopropylsulfonyl)phenyl)-3-(3-phenyl-4,5-dihydroisoxazol-5-yl)pyrazin-2-amine

HRID 78691노트

반응식

HRID 78691 반응식
[CH:1]([S:4]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]=[C:15]([CH:20]=[CH2:21])[C:16]([NH2:19])=[N:17][CH:18]=2)=[CH:9][CH:8]=1)(=[O:6])=[O:5])([CH3:3])[CH3:2].[OH:22]/[N:23]=[C:24](\Cl)/[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CN(C)C=O.C(OCC)(=O)C.O>[CH:1]([S:4]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]=[C:15]([CH:20]3[O:22][N:23]=[C:24]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH2:21]3)[C:16]([NH2:19])=[N:17][CH:18]=2)=[CH:9][CH:8]=1)(=[O:5])=[O:6])([CH3:3])[CH3:2]

참가 물질

6

반응물 2

HCID 5706359Alpha-chlorobenzaldoximeHCID 866827695-(4-(Isopropylsulfonyl)phenyl)-3-vinylpyrazin-2-amine

생성물 1

HCID 715219955-(4-(Isopropylsulfonyl)phenyl)-3-(3-phenyl-4,5-dihydroisoxazol-5-yl)pyrazin-2-amine수율 29%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To solution of 5-(4-isopropylsulfonylphenyl)-3-vinyl-pyrazin-2-amine (20 mg, 0.06592 mmol) in N,N-dimethylformamide (2 mL) was added (Z)—N-hydroxybenzimidoyl chloride (13.33 mg, 0.08570 mmol) followed by TEA (20.02 mg, 27.58 μL, 0.1978 mmol) added drop wise. The reaction mixture was stirred at ambient temperature for 20 mins followed by heating to 65° C. for 1 hour. The reaction mixture was cooled to room temperature and diluted with ethyl acetate (5 mL) and water (5 mL) and the layers separated. The aqueous layer was extracted further with ethyl acetate (2×5 mL) and the combined organic extracts washed with water (3×10 mL), dried over MgSO4 and concentrated in vacuo to a solid. Purification by fractionlynx yielded 5-(4-(isopropylsulfonyl)phenyl)-3-(3-phenyl-4,5-dihydroisoxazol-5-yl)pyrazin-2-amine Compound I-1. (10.4 mg, 29% Yield). DMSO 1.15 (6H,d), 3.4-3.48 (1H,m) 3.7-3.8 (1H,m), 4.28 (1H,dd), 6.02 (1H,dd), 6.95 (2H,brs), 7.48-7.53 (3H,m), 7.78-7.85 (4H,m), 8.2 (2H,d), 8.75 (1H,s); LC/MS m/z 423.4 [M+H]+.

후처리

  1. additionadded drop wise
  2. temperatureby heating to 65° C. for 1 hour
  3. temperatureThe reaction mixture was cooled to room temperature
  4. customthe layers separated
  5. extractionThe aqueous layer was extracted further with ethyl acetate (2×5 mL)
  6. washthe combined organic extracts washed with water (3×10 mL)
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo to a solid
  9. customPurification by fractionlynx

출처 및 근거

ORD 기록
ord-7c6cea91e3d84b388426a5c424f71d9e
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841450B2

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