HCID 86727482, compound → HCID 86727483, compound

HRID 519106Notes

Reaction equation

HRID 519106 reaction equation
[CH2:1]([O:8][C:9]1[CH:22]=[C:21]2[C:12]([N:13]3[C:18]([CH2:19][O:20]2)=[N:17][NH:16][C:15](=[O:23])[CH:14]3[CH3:24])=[CH:11][C:10]=1[N+:25]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.[Ni]>[NH2:25][C:10]1[CH:11]=[C:12]2[C:21](=[CH:22][C:9]=1[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[O:20][CH2:19][C:18]1[N:13]2[CH:14]([CH3:24])[C:15](=[O:23])[NH:16][N:17]=1

Participants

4

Reactant 1

HCID 86727482HCID 86727482, compound

Product 1

HCID 86727483HCID 86727483, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a solution of 7-benzyloxy-4-methyl-6-nitro-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (0.14 g, 0.38 mmol) in MeOH (10 mL) was added Raney-Ni (0.03 g). Then the mixture was stirred under an atmosphere of H2 (1 atm) at rt for 2 h. The reaction mixture was filtered and washed with 10% MeOH/DCM (3×10 mL). The filtrate was concentrated in vacuo to give 6-amino-7-benzyloxy-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (0.065 g, 54%), which was used in the next step directly without further purification. TLC (eluting with 50% EtOAc in petroleum ether) Rf=0.3.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed with 10% MeOH/DCM (3×10 mL)
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-7c4c67da3d484059b8dc31c746467368
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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