Ammonium formate → HCID 44546067, compound

HRID 1958660Notes

Reaction equation

HRID 1958660 reaction equation
[F:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][C:7]2[NH:8][C:9]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[N:23]=3)=[C:10]([C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[N:18]=[CH:17][CH:16]=[CH:15]4)[N:11]=2)=[CH:4][C:3]=1[N+:31]([O-])=O.C([O-])=O.[NH4+]>CO.[Pd]>[F:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][C:7]2[NH:8][C:9]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[N:23]=3)=[C:10]([C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[N:18]=[CH:17][CH:16]=[CH:15]4)[N:11]=2)=[CH:4][C:3]=1[NH2:31]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 44545793HCID 44545793, compound

Product 1

HCID 44546067HCID 44546067, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of 6-(2-(4-fluoro-3-nitrobenzyl)-5-(6-methylpyridin-2-yl)-1H-imidazol-4-yl)quinoline (Example 72, prepared according to the method described in US 2008/0319012 A1) (448 mg, 1.02 mmol) in MeOH (30 mL) were added ammonium formate (257 mg, 4.08 mmol) and 10% Pd/C (30 mg) and the mixture was stirred at room temperature for 100 min. The reaction mixture was filtered through celite and the filtrate was concentrated under reduced pressure. The residue was diluted with H2O (50 mL) and added 2N HCl solution until all remaining substances were dissolved. The aqueous solution was neutralized by addition of NH4OH solution to pH 7. The precipitate was filtered, washed with H2O, and dried under vacuum. The precipitate was purified by MPLC (MeOH:CH2Cl2=1:20 (v/v) to 1:15 (v/v)) to afford the title compound (445.5 mg, 80%). 1H NMR (300 MHz, CDCl3) δ 2.50 (3H, s), 4.10 (2H, s), 6.64-6.72 (2H, m), 6.92 (1H, d), 6.95 (1H, d), 7.24 (1H, s), 7.35-7.39 (1H, m), 7.41 (1H, dd), 7.96 (1H, dd), 8.10 (1H, d), 8.14-8.17 (2H, m), 8.91 (1H, dd). MS (ESI) m/z 410 (MH+).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionThe residue was diluted with H2O (50 mL)
  4. additionadded 2N HCl solution until all remaining substances
  5. dissolutionwere dissolved
  6. additionThe aqueous solution was neutralized by addition of NH4OH solution to pH 7
  7. filtrationThe precipitate was filtered
  8. washwashed with H2O
  9. customdried under vacuum
  10. customThe precipitate was purified by MPLC (MeOH:CH2Cl2=1:20 (v/v) to 1:15 (v/v))

Sources & evidence

ORD record
ord-e08ab73c801e4f8d847aa8a3a738a858
Source dataset
uspto-grants-2013_04
Patent number
US08410146B2

Reaction notes

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