Sodium Bicarbonate → HCID 66744433、化合物

HRID 1959394

反応式

HRID 1959394 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

HCID 66744433HCID 66744433、化合物収率 6%

試薬・触媒・溶媒 1

HCID 1118Sulfuric Acid溶媒

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-c523891bce054fcdab0d1a0484ae5983
出典データセット
uspto-grants-2013_04
特許番号
US08410112B2

関連ノート

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