HCID 86704554, compound → HCID 86704553, compound

HRID 633466Notes

Reaction equation

HRID 633466 reaction equation
[CH3:1][N:2]1[C:20](=[O:21])[N:5]2[C:6]3[CH:16]=[C:15]([N+:17]([O-])=O)[CH:14]=[CH:13][C:7]=3[O:8][CH2:9][C:10]3([CH2:12][O:11]3)[C:4]2=[N:3]1>CO.[Pd]>[NH2:17][C:15]1[CH:14]=[CH:13][C:7]2[O:8][CH2:9][C:10]([OH:11])([CH3:12])[C:4]3[N:5]([C:20](=[O:21])[N:2]([CH3:1])[N:3]=3)[C:6]=2[CH:16]=1

Participants

4

Reactant 1

HCID 86704554HCID 86704554, compound

Product 1

HCID 86704553HCID 86704553, compoundYield 88.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-Methyl-9-nitro-5H-spiro[benzo[b][1,2,4]triazolo[4,3-d][1,4]oxazepine-4,2′-oxiran]-1(2H)-one (250 mg) and 10% Pd—C were suspended in methanol (10 mL). The reaction mixture was shaken at room temperature under H2 atmosphere (30 psi) for one hour. The catalyst was filtered off over celite and washed with methanol (5×50 mL). The filtrate was evaporated to give 9-amino-4-hydroxy-2,4-dimethyl-4,5-dihydrobenzo[b][1,2,4]triazolo[4,3-d][1,4]oxazepin-1(2H)-one (200 mg). m/z=263.12 (M+H)+.

Workup

  1. filtrationThe catalyst was filtered off over celite
  2. washwashed with methanol (5×50 mL)
  3. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-65f7b310b9e3449db602e6a58b3e9550
Source dataset
uspto-grants-2016_04
Patent number
US09321763B2

Reaction notes

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