Acetonitrile → 3-[5-[4-(Aminomethyl)phenyl]-1,3,4-oxadiazol-2-yl]-5-(4-isopropylsulfonylphenyl)pyrazin-2-amine

HRID 78646

반응식

HRID 78646 반응식
[NH2:1][C:2]1[C:3]([C:20]2[O:24][C:23]([C:25]3[CH:30]=[CH:29][C:28]([CH2:31][NH:32]C(=O)OC(C)(C)C)=[CH:27][CH:26]=3)=[N:22][N:21]=2)=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH:17]([CH3:19])[CH3:18])(=[O:16])=[O:15])=[CH:10][CH:9]=2)=[CH:6][N:7]=1.C(O)(C(F)(F)F)=O.C(#N)C>C(Cl)Cl>[NH2:32][CH2:31][C:28]1[CH:29]=[CH:30][C:25]([C:23]2[O:24][C:20]([C:3]3[C:2]([NH2:1])=[N:7][CH:6]=[C:5]([C:8]4[CH:13]=[CH:12][C:11]([S:14]([CH:17]([CH3:18])[CH3:19])(=[O:16])=[O:15])=[CH:10][CH:9]=4)[N:4]=3)=[N:21][N:22]=2)=[CH:26][CH:27]=1

참가 물질

5

반응물 3

HCID 6342AcetonitrileHCID 6422Trifluoroacetic acidHCID 59471911Tert-butyl 4-(5-(3-amino-6-(4-(isopropylsulfonyl)phenyl)pyrazin-2-yl)-1,3,4-oxadiazol-2-yl)benzylcarbamate

생성물 1

HCID 594722763-[5-[4-(Aminomethyl)phenyl]-1,3,4-oxadiazol-2-yl]-5-(4-isopropylsulfonylphenyl)pyrazin-2-amine수율 48.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of tert-butyl N-[[4-[5-[3-amino-6-(4-isopropylsulfonylphenyl)pyrazin-2-yl]-1,3,4-oxadiazol-2-yl]phenyl]methyl]carbamate (45 mg, 0.08172 mmol) in CH2Cl2 (1 mL) was treated with TFA (1 mL, 12.98 mmol) and stirred at room temperature for 1 h. The solution was concentrated under reduced pressure then azeotroped with methanol/ CH2Cl2 (×2), dissolved in CH2Cl2/MeOH and passed through a carbonate cartridge. The eluent was concentrated then crystallised from hot acetonitrile giving a yellow crystalline solid (18 mg, 41% yield); 1H NMR (400 MHz, DMSO) d 1.20 (d, 6H), 1.97 (br s, 2H), 3.47 (m, 1H), 3.85 (s, 2H), 7.63 (d, 2H), 7.89 (br s, 2H), 7.98 (d, 2H), 8.11 (d, 2H), 8.40 (d, 2H) and 9.06 (s, 1H) ppm; MS (ES+) 451.41

후처리

  1. concentrationThe solution was concentrated under reduced pressure
  2. customthen azeotroped with methanol/ CH2Cl2 (×2)
  3. dissolutiondissolved in CH2Cl2/MeOH
  4. concentrationThe eluent was concentrated

출처 및 근거

ORD 기록
ord-c4b40bd2050e4a8bb1c65c8fd6798e5a
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841308B2

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