HCID 20079495, compound → HCID 9837440, compound

HRID 1654063Notes

Reaction equation

HRID 1654063 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][C:5]=1[NH:10][C:11]1[CH:19]=[C:18]2[C:14]([CH:15]=[N:16][NH:17]2)=[CH:13][CH:12]=1)([O-])=O>C(O)C.O=[Pt]=O>[NH2:1][C:4]1[CH:9]=[CH:8][N:7]=[CH:6][C:5]=1[NH:10][C:11]1[CH:19]=[C:18]2[C:14]([CH:15]=[N:16][NH:17]2)=[CH:13][CH:12]=1

Participants

4

Reactant 1

HCID 20079495HCID 20079495, compound

Product 1

HCID 9837440HCID 9837440, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent2×

Procedure

To PtO2 (0.3 g) in 10 ml of ethanol was added N-(4-nitro-3-pyridinyl)-1H-indazol-6-amine, N6 -oxide (2.0 g) in 240 ml of ethanol and this was hydrogenated on a Parr apparatus at 60 psi for 20 hours. The mixture was filtered and concentrated to an oil (2.1 g). This material was eluted with 20% methanol/DCM on a silica gel column via HPLC. The desired fractions were concentrated to a solid (0.7 g), which was recrystallized from acetonitrile to yield a solid 0.5 g, m.p. 214°-216° C.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated to an oil (2.1 g)
  3. washThis material was eluted with 20% methanol/DCM on a silica gel column via HPLC
  4. concentrationThe desired fractions were concentrated to a solid (0.7 g), which
  5. customwas recrystallized from acetonitrile

Sources & evidence

ORD record
ord-a0d60229830d44548f338b3eb64795e5
Source dataset
uspto-grants-1995_04
Patent number
US05405856

Reaction notes

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