Hydrochloric Acid → HCID 90409483, compound

HRID 589049Notes

Reaction equation

HRID 589049 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]1[N:12]2[C:13](=[O:19])[NH:14][C:15]3=[CH:16][CH:17]=[CH:18][C:10](=[C:11]23)[O:9][CH2:8]1.Cl.O>CO>[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[CH:7]1[N:12]2[C:13](=[O:19])[NH:14][C:15]3=[CH:16][CH:17]=[CH:18][C:10](=[C:11]23)[O:9][CH2:8]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 90410438HCID 90410438, compound

Product 1

HCID 90409483HCID 90409483, compoundYield 82.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The tricycle intermediate, 4-pyridin-2-yl-4,5-dihydroimidazo[1,5,4-de][1,4]benzoxazin-2(1H)-one (0.25 g, 0.98 mmol) from Example 13, was partially dissolved in methanol (50.0 mL) and 12.0 M hydrogen chloride in water (1.0 mL, 12 mmol) in a Parr bottle. The reaction was degassed with nitrogen, followed by addition of palladium (10% on carbon), and the reaction was charged to 55 PSI hydrogen and shaken for 6 days. The reaction was filtered to remove the catalyst and concentrated in vacuo to give 4-piperidin-2-yl-4,5-dihydroimidazo[1,5,4-de][1,4]benzoxazin-2(1H)-one as a dark oil (0.21 g, 82%). LCMS calculated for C14H18N3O2 (M+H)+: m/z=260.1. found: 260.1.

Workup

  1. customThe reaction was degassed with nitrogen
  2. additionfollowed by addition of palladium (10% on carbon)
  3. additionthe reaction was charged to 55 PSI hydrogen
  4. filtrationThe reaction was filtered
  5. customto remove the catalyst
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b071f2cb254245b7a49340f8a3e8d7e4
Source dataset
uspto-grants-2016_01
Patent number
US09227985B2

Reaction notes

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