Ethanol → 3-(5-Cyclopropyl-1H-pyrazol-3-yl)-N-[(1S)-1-(5-fluoropyridin-2-yl)ethyl]-3H-imidazo[4,5-b]pyridin-5-amine

HRID 450396ノート

反応式

HRID 450396 の反応式
[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH:9][C:10]3[C:15]([N+:16]([O-])=O)=[CH:14][CH:13]=[C:12]([NH:19][C@H:20]([C:22]4[CH:27]=[CH:26][C:25]([F:28])=[CH:24][N:23]=4)[CH3:21])[N:11]=3)[CH:5]=2)[CH2:3][CH2:2]1.[CH2:29](O)C.C(O)(=O)C.C(N)=N.C(OCC)(=O)C>[Cl-].[Na+].O.[Pd]>[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([N:9]3[C:10]4=[N:11][C:12]([NH:19][C@H:20]([C:22]5[CH:27]=[CH:26][C:25]([F:28])=[CH:24][N:23]=5)[CH3:21])=[CH:13][CH:14]=[C:15]4[N:16]=[CH:29]3)[CH:5]=2)[CH2:3][CH2:2]1

参加物

7

反応物 4

HCID 702EthanolHCID 8857Ethyl AcetateHCID 160693Formamidine acetateHCID 86649276N2-(5-Cyclopropyl-1H-pyrazol-3-yl)-N6-[(1S)-1-(5-fluoropyridin-2-yl)ethyl]-3-nitropyridine-2,6-diamine2 回

生成物 1

HCID 251159633-(5-Cyclopropyl-1H-pyrazol-3-yl)-N-[(1S)-1-(5-fluoropyridin-2-yl)ethyl]-3H-imidazo[4,5-b]pyridin-5-amine

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 57417360Sodium chloride; water溶媒

実験手順

N2-(5-cyclopropyl-1H-pyrazol-3-yl)-N6-[(1S)-1-(5-fluoropyridin-2-yl)ethyl]-3-nitropyridine-2,6-diamine (Intermediate 10, 0.4 g) was dissolved into ethanol (20 mL) with Pd—C (60 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 95° 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 silica gel column (Ethyl acetate/MeOH) to afford 0.16 g of the title compound. MS (electrospray): 364 (M+1) for C19H18FN7. 1H NMR (300 MHz, CD3OD) δ ppm 8.45 (s, 1H) 8.30 (s, 1H) 7.70 (d, 1H) 7.50 (d, 1H) 6.70 (d, 1H) 6.20 (s, 1H) 5.10 (dd, 1H) 2.00 (m, 1H) 1.55 (d, 3H) 1.00 (m, 2H) 0.80 (m, 2H).

後処理

  1. filtrationafter the filtration
  2. customof resulting mixture
  3. stirringThe mixture was stirred at 95° 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 silica gel column (Ethyl acetate/MeOH)

出典と根拠

ORDレコード
ord-f18f5bb4c198444c998d53a4012fbca7
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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