Sodium Bicarbonate → HCID 66744433, 화합물

HRID 1959394

반응식

HRID 1959394 반응식
[NH2:1][C:2]1[C:3]([C:19]([NH:21][CH2:22][C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=O)=[O:20])=[N:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([S:14]([CH2:17][CH3:18])(=[O:16])=[O:15])[CH2:10][CH2:9]2)=[CH:6][N:7]=1.C([O-])(O)=O.[Na+]>OS(O)(=O)=O>[CH2:17]([S:14]([N:11]1[CH2:10][CH2:9][N:8]([C:5]2[N:4]=[C:3]([C:19]3[O:20][C:23]([C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)=[CH:22][N:21]=3)[C:2]([NH2:1])=[N:7][CH:6]=2)[CH2:13][CH2:12]1)(=[O:15])=[O:16])[CH3:18]

참가 물질

4

반응물 2

HCID 516892Sodium BicarbonateHCID 667454513-amino-6-(4-ethylsulfonylpiperazin-1-yl)-N-phenacyl-pyrazine-2-carboxamide

생성물 1

HCID 66744433HCID 66744433, 화합물수율 6%

시약·촉매·용매 1

HCID 1118Sulfuric Acid용매

실험 절차

3-amino-6-(4-ethylsulfonylpiperazin-1-yl)-N-phenacyl-pyrazine-2-carboxamide (80 mg, 0.1850 mmol) in H2SO4 (1.5 mL) was stirred at ambient temperature for 16 hours. The reaction was neutralised by addition of NaHCO3 solution and then extracted with EtOAc (3×), combined organics dried (MgSO4) and concentrated in vacuo. The resultant residue was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 uM, 100A column, gradient 10%-95% B (solvent A: 0.05% TFA in water, solvent B: CH3CN) over 16 minutes at 25 mL/min]. The fractions were collected and freeze-dried to give the title compound as an orange solid (4.5 mg, 6% Yield). 1H NMR (DMSO) d 1.25 (3H, t), 3.11 (2H, q), 3.35 masked signal, 3.54 (4H, m), 7.00 (2H, br s), 7.42 (1H, m), 7.53 (2H, m), 7.84 (2H, m), 7.99 (1H, s), 8.14 (1H, s) ppm; MS (ES+) 415.0

후처리

  1. extractionextracted with EtOAc (3×)
  2. dry with materialcombined organics dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe resultant residue was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 uM, 100A column, gradient 10%-95% B (solvent A: 0.05% TFA in water, solvent B: CH3CN) over 16 minutes at 25 mL/min]
  5. customThe fractions were collected
  6. customfreeze-dried

출처 및 근거

ORD 기록
ord-c523891bce054fcdab0d1a0484ae5983
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08410112B2

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