Acetic Acid → HCID 66919054, compound

HRID 2354224Notes

Reaction equation

HRID 2354224 reaction equation
[CH:1]1([NH:4][C:5](=[O:31])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([N:13]3[C:22](=[O:23])[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([C:24]5[CH2:25][CH2:26][N:27]([CH3:30])[CH2:28][CH:29]=5)[CH:20]=4)[N:15]=[CH:14]3)[CH:7]=2)[CH2:3][CH2:2]1.C(O)(=O)C>[Pd].C(O)C>[CH:1]1([NH:4][C:5](=[O:31])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([N:13]3[C:22](=[O:23])[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([CH:24]5[CH2:25][CH2:26][N:27]([CH3:30])[CH2:28][CH2:29]5)[CH:20]=4)[N:15]=[CH:14]3)[CH:7]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 66918964HCID 66918964, compound

Product 1

HCID 66919054HCID 66919054, compoundYield 49.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

N-Cyclopropyl-4-methyl-3-[6-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-4-oxoquinazolin-3(4H)-yl]benzamide (0.284 g) and 10% Palladium on carbon (0.028 g) were stirred in ethanol (6 ml) and acetic acid (0.5 ml) under an atmosphere of hydrogen for 24 hours. The catalyst was removed by filtration through diatomaceous earth (Celite®) and the filtrate was concentrated under reduced pressure. Purification by column chromatography on a silica column eluting with 10% methanol/ethyl acetate+1% aqueous ammonia solution to give the title compound (0.140 g) as a white foam solid; NMR Spectrum: (DMSOd6) 0.56 (m, 2H), 0.69 (m, 2H), 1.78 (m, 4H), 2.00 (m, 2H), 2.13 (s, 3H), 2.20 (s, 3H), 2.67 (m, 1H), 2.88 (m, 3H), 7.52 (d, 1H), 7.71 (d, 1H), 7.82 (m, 2H), 7.90 (d, 1H), 8.02 (s, 1H), 8.24 (s, 1H), 8.42 (d, 1H); Mass Spectrum: M+H+ 417.

Workup

  1. customThe catalyst was removed by filtration through diatomaceous earth (Celite®)
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customPurification by column chromatography on a silica column
  4. washeluting with 10% methanol/ethyl acetate+1% aqueous ammonia solution

Sources & evidence

ORD record
ord-ceafeaa439554226aca851035d120861
Source dataset
uspto-grants-2010_07
Patent number
US07750154B2

Reaction notes

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