HCID 90410261, compound → HCID 90408833, compound

HRID 589056Notes

Reaction equation

HRID 589056 reaction equation
[N+:1]([C:4]1[C:9]2[N:10]3[CH2:14][C:11]3([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[CH2:12][O:13][C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-])=O.[H][H]>CO.O1CCCC1.[Pd]>[CH3:14][C:11]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[NH:10][C:9]2=[C:4]([NH2:1])[CH:5]=[CH:6][CH:7]=[C:8]2[O:13][CH2:12]1

Participants

6

Reactant 2

HCID 90410261HCID 90410261, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 90408833HCID 90408833, compoundYield 31.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 7-nitro-1a-pyridin-2-yl-1a,2-dihydro-1H-azireno[2,1-c][1,4]benzoxazine (100 mg, 0.4 mmol) in methanol (6 mL) and tetrahydrofuran (2 mL) was degassed with nitrogen in a Parr bottle followed by addition of palladium (10% on carbon) (30 mg, 0.28 mmol). The reaction was charged with hydrogen to 40 psi and shaken for 6 hrs. The reaction was filtered and concentrated to give crude 3-methyl-3-pyridin-2-yl-3,4-dihydro-2H-1,4-benzoxazin-5-amine (0.030 g. 30%). LCMS calculated for C14H16N3O (M+H)+: m/z=242.1. found: 242.1.

Workup

  1. customwas degassed with nitrogen in a Parr bottle
  2. filtrationThe reaction was filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-f95a2296fcb44af2a894ca57b720df66
Source dataset
uspto-grants-2016_01
Patent number
US09227985B2

Reaction notes

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