MeOH tetrahydrofuran → HCID 59619790, compound

HRID 445673Notes

Reaction equation

HRID 445673 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([N:7]2[C:19]3[C:18]4[CH:17]=[C:16]([C:20]5[CH:21]=[N:22][C:23](NCCO)=[CH:24][CH:25]=5)[CH:15]=[CH:14][C:13]=4[N:12]=[CH:11][C:10]=3[N:9]([CH3:30])[C:8]2=[O:31])[C:4]([CH3:32])=[N:3]1.C[OH:34].[CH2:35]1[CH2:39][O:38]CC1>[Pd]>[CH3:1][N:2]1[CH:6]=[C:5]([N:7]2[C:19]3[C:18]4[CH:17]=[C:16]([C:20]5[CH:21]=[N:22][C:23]([O:38][CH2:39][CH2:35][OH:34])=[CH:24][CH:25]=5)[CH:15]=[CH:14][C:13]=4[N:12]=[CH:11][C:10]=3[N:9]([CH3:30])[C:8]2=[O:31])[C:4]([CH3:32])=[N:3]1

Participants

4

Reactant 2

HCID 21899815MeOH tetrahydrofuranHCID 59619625HCID 59619625, compound

Product 1

HCID 59619790HCID 59619790, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a mixture of 1-(1,3-Dimethyl-1H-pyrazol-4-yl)-8-[6-(2-hydroxy-ethylamino)-pyridin-3-yl]-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one (Example 19, 40 mg, 0.077 mmol) in MeOH/THF=1:1 (4 ml) was added under nitrogen Pd/C 10% (20 mg, 0.026 mmol). The RM was shacked under H2 at rt for 22 h. The reaction was not completed, again Pd/C catalyst (20 mg) was added and the mixture was stirred under H2 at rt for 22 h. This procedure was repeated for a third time. Then the suspension was filtered over celite and washed with MeOH. The filtrate was evaporated. The residue was dissolved in MeOH and purified directly by Prep.HPLC (H2O (0.1% TFA)/CH3CN 95:5 to 65:35). The fractions containing product were collected together and basified with NaHCO3 (0.3 g), before being concentrated. The resulting suspension was filtered and the cake was washed with water, before being dried under high vacuum to give the title compound as a white solid. (HPLC: tR 2.32 min (Method A); M+H=431 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 8.97 (s, 1H), 8.30-8.26 (m, 1H), 8.17-8.06 (m, 2H), 7.93-7.86 (m, 1H), 7.81-7.75 (m, 1H), 7.50-7.46 (m, 1H), 6.97-6.91 (m, 1H), 4.80-4.86 (m, 1H), 4.34-4.28 (m, 2H), 3.92 (s, 31-1), 3.75-3.69 (m, 2H), 3.58 (s, 3H), 1.95 (s, 3H))

Workup

  1. additionwas added under nitrogen Pd/C 10% (20 mg, 0.026 mmol)
  2. filtrationThen the suspension was filtered over celite
  3. washwashed with MeOH
  4. customThe filtrate was evaporated
  5. dissolutionThe residue was dissolved in MeOH
  6. custompurified directly by Prep.HPLC (H2O (0.1% TFA)/CH3CN 95:5 to 65:35)
  7. additionThe fractions containing product
  8. customwere collected together
  9. concentrationbefore being concentrated
  10. filtrationThe resulting suspension was filtered
  11. washthe cake was washed with water
  12. custombefore being dried under high vacuum

Sources & evidence

ORD record
ord-e3500a5978ec441fa64062f7bdca0592
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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