Ethanol → HCID 178458593、化合物

HRID 450401ノート

反応式

HRID 450401 の反応式
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[C:14]([NH:21][C:22]3[CH:26]=[C:25]([O:27][CH:28]([CH3:30])[CH3:29])[NH:24][N:23]=3)[N:13]=2)[CH2:9][OH:10])=[N:6][CH:7]=1.[CH2:31](O)C.C(O)(=O)C.C(N)=N.C(OCC)(=O)C>[Cl-].[Na+].O.[Pd]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]([NH:11][C:12]2[N:13]=[C:14]3[N:21]([C:22]4[CH:26]=[C:25]([O:27][CH:28]([CH3:30])[CH3:29])[NH:24][N:23]=4)[CH:31]=[N:18][C:15]3=[CH:16][CH:17]=2)[CH2:9][OH:10])=[N:6][CH:7]=1

参加物

7

反応物 4

HCID 702EthanolHCID 8857Ethyl AcetateHCID 160693Formamidine acetateHCID 178458670HCID 178458670、化合物2 回

生成物 1

HCID 178458593HCID 178458593、化合物

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 57417360Sodium chloride; water溶媒

実験手順

(2R)-2-(5-fluoropyridin-2-yl)-2-({6-[(5-isopropoxy-1H-pyrazol-3-yl)amino]-5-nitropyridin-2-yl}amino)ethanol (Intermediate 24, 0.45 g) was dissolved into ethanol (20 mL) with Pd—C (90 mg) and a hydrogen inlet. The mixture was stirred at room temperature until no starting material was detected with TLC or LCMS. Formamidine acetate (0.5 g) was added to the filtrate after the filtration of resulting mixture. The mixture was stirred at 85° C. for 4 hours. Ethyl acetate (40 mL) was added into the resulting mixture, and brine (10 mL×3) was used to wash the organic layer. The organic layer was dried and concentrated. The resulting residue was separated by a silica gel column (Ethyl acetate/MeOH) to afford 0.075 g of the title compound. MS (electrospray): 398 (M+1) for C19H20FN7O2. 1H NMR (300 MHz, CD3OD) δ ppm 8.50 (d, 1H) 8.30 (s, 1H) 7.80 (d, 1H) 7.50 (dd, 1H) 6.70 (d, 1H) 6.05 (s, 1H) 5.20 (m, 1H) 4.65 (m, 1H) 4.00 (m, 2H), 1.55-1.35 (m, 6H).

後処理

  1. filtrationafter the filtration
  2. customof resulting mixture
  3. stirringThe mixture was stirred at 85° C. for 4 hours
  4. washto wash the organic layer
  5. customThe organic layer was dried
  6. concentrationconcentrated
  7. customThe resulting residue was separated by a silica gel column (Ethyl acetate/MeOH)

出典と根拠

ORDレコード
ord-aefffef5313f4728a8206d8154b15371
出典データセット
uspto-grants-2013_07
特許番号
US08486966B2

反応ノート

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