HCID 66758785, compound → HCID 66758969, compound

HRID 1442048Notes

Reaction equation

HRID 1442048 reaction equation
[CH2:1]([C:3]1[N:11]2[C:6]([CH2:7][O:8][C:9]3[C:15]([N+:16]([O-])=O)=[CH:14][CH:13]=[CH:12][C:10]=32)=[C:5]([C:19]([OH:21])=[O:20])[N:4]=1)[CH3:2]>CO>[CH2:1]([C:3]1[N:11]2[C:6]([CH2:7][O:8][C:9]3[C:15]([NH2:16])=[CH:14][CH:13]=[CH:12][C:10]=32)=[C:5]([C:19]([OH:21])=[O:20])[N:4]=1)[CH3:2]

Participants

3

Reactant 1

HCID 66758785HCID 66758785, compound

Product 1

HCID 66758969HCID 66758969, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 6-Nitro-3-carboxy-4H-imidazo[5,1-c]-1,4-benzoxazine was reduced shaken in MeOH under 40 p.s.i. H2 with 20 weight percent of 10% Pd/C (Degussa) for 1 h then filtered and the solvent evaporated. The compound was purified directly by column chromatograph (EtOAc/hexane) to yield Ethyl 6-Amino-3-carboxy-4H-imidazo[5,1-c]-1,4-benzoxazine 1H (DMSO-d6) 8.41 (s, 1H), 6.98 (m, 1H), 6.82 (m, 1H), 6.43 (m, 1H), 5.28 ((s. 2H), 4.23 (q, 2H, J=6.2 Hz), 1.27 (t, 2H, J=6.2 Hz) purity 92% MS (m/e): 232 (MH+).

Workup

  1. filtrationH2 with 20 weight percent of 10% Pd/C (Degussa) for 1 h then filtered
  2. customthe solvent evaporated
  3. customThe compound was purified directly by column chromatograph (EtOAc/hexane)

Sources & evidence

ORD record
ord-bf1e1ddaef2c484d907cdefd7640a12d
Source dataset
uspto-grants-2010_02
Patent number
US07655797B2

Reaction notes

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