Ethanol → HCID 178458589, compound

HRID 450408Notes

Reaction equation

HRID 450408 reaction equation
[Cl:1][C:2]1[C:3]([NH:21][C@H:22]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][N:25]=2)[CH3:23])=[N:4][C:5]([NH:11][C:12]2[CH:16]=[C:15]([O:17][CH:18]([CH3:20])[CH3:19])[NH:14][N:13]=2)=[C:6]([N+:8]([O-])=O)[CH:7]=1.[CH2:31](O)C.C(OCC)(=O)C>[Cl-].[Na+].O.[Pd]>[Cl:1][C:2]1[CH:7]=[C:6]2[N:8]=[CH:31][N:11]([C:12]3[CH:16]=[C:15]([O:17][CH:18]([CH3:20])[CH3:19])[NH:14][N:13]=3)[C:5]2=[N:4][C:3]=1[NH:21][C@H:22]([C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][N:25]=1)[CH3:23]

Participants

6

Reactant 3

HCID 702EthanolHCID 8857Ethyl AcetateHCID 178458652HCID 178458652, compound2×

Product 1

HCID 178458589HCID 178458589, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 57417360Sodium chloride; waterSolvent

Procedure

3-Chloro-N2-[(1S)-1-(5-fluoropyridin-2-yl)ethyl]-N6-(5-isopropoxy-1H-pyrazol-3-yl)-5-nitropyridine-2,6-diamine (Intermediate 39, 0.5 g) was dissolved into ethanol (20 mL) with Pd—C (150 mg) and a hydrogen inlet. The mixture was stirred at room temperature until no starting material was detected with TLC or LCMS. Formylamidine 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 silica gel column (Ethyl acetate/MeOH) to afford 0.12 g desired product. MS (electrospray): 416 (M+1) for C19H19ClFN7O. 1H NMR (300 MHz, CD3OD) δ ppm 8.40 (s, 1H) 8.30 (s, 1H) 7.90 (d, 1H) 7.50 (m 2H) 6.70 (d, 1H) 6.00 (s, 1H) 5.40 (m, 1H) 4.60 (m, 1H) 1.60 (d, 3H) 1.40 (d, 6H).

Workup

  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 silica gel column (Ethyl acetate/MeOH)

Sources & evidence

ORD record
ord-95a04e8d24374fc9aa602f36aac1f3e2
Source dataset
uspto-grants-2013_07
Patent number
US08486966B2

Reaction notes

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