Dimethylformamide → 3-[5-[3-[(Dimethylamino)methyl]phenyl]-1,3,4-oxadiazol-2-yl]-5-(4-propan-2-ylsulfonylphenyl)pyrazin-2-amine

HRID 2204859노트

반응식

HRID 2204859 반응식
NC[C:3]1[CH:4]=[C:5]([C:9]2[O:13][C:12]([C:14]3[C:15]([NH2:32])=[N:16][CH:17]=[C:18]([C:20]4[CH:25]=[CH:24][C:23]([S:26]([CH:29]([CH3:31])[CH3:30])(=[O:28])=[O:27])=[CH:22][CH:21]=4)[N:19]=3)=[N:11][N:10]=2)[CH:6]=[CH:7][CH:8]=1.CI.C(=O)([O-])[O-].[K+].[K+].[CH3:41][N:42]([CH:44]=O)[CH3:43]>C(OCC)(=O)C>[CH3:43][N:42]([CH2:44][C:3]1[CH:4]=[C:5]([C:9]2[O:13][C:12]([C:14]3[C:15]([NH2:32])=[N:16][CH:17]=[C:18]([C:20]4[CH:25]=[CH:24][C:23]([S:26]([CH:29]([CH3:30])[CH3:31])(=[O:27])=[O:28])=[CH:22][CH:21]=4)[N:19]=3)=[N:11][N:10]=2)[CH:6]=[CH:7][CH:8]=1)[CH3:41]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 594716333-[5-[3-(Aminomethyl)phenyl]-1,3,4-oxadiazol-2-yl]-5-(4-isopropylsulfonylphenyl)pyrazin-2-amine

생성물 1

HCID 594722773-[5-[3-[(Dimethylamino)methyl]phenyl]-1,3,4-oxadiazol-2-yl]-5-(4-propan-2-ylsulfonylphenyl)pyrazin-2-amine수율 24%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

3-[5-[3-(aminomethyl)phenyl]-1,3,4-oxadiazol-2-yl]-5-(4-isopropylsulfonylphenyl)pyrazin-2-amine (12 mg, 0.02108 mmol) was added to a solution of MeI (8.976 mg, 3.937 μL, 0.06324 mmol) and potassium carbonate (8.740 mg, 0.06324 mmol) in DMF (2 mL). The resulting mixture was stirred at room temperature for 30 min. The reaction mixture was diluted with ethyl acetate (3 mL) and washed successively with water (1×5 mL) and brine (1×5 mL). The organic extracts were dried over MgSO4 and concentrated in vacuo. The residue was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 μM, 100 Å column, gradient 10%-95% B (solvent A: 0.05% TFA in water; solvent B: CH3CN) over 16 minutes at 25 mL/min]. Product fractions were combined and lypholised to give the product as a yellow solid (3.0 mg, 24% yield); 1H NMR (400 MHz, MeOD) d 1.35-1.4 (m, 6H), 2.95 (s, 6H), 4.65 (s, 2H), 7.8-7.85 (m, 2H), 8.05-8.1 (m, 2H), 8.4-8.5 (m, 4H) and 9.95 (s, 1H) ppm; MS (ES+) 479.3

후처리

  1. washwashed successively with water (1×5 mL) and brine (1×5 mL)
  2. dry with materialThe organic extracts were dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 μM, 100 Å column, gradient 10%-95% B (solvent A: 0.05% TFA in water; solvent B: CH3CN) over 16 minutes at 25 mL/min]

출처 및 근거

ORD 기록
ord-9bd51224c49b4a1e9233b4bd3c4f41f7
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09365557B2

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