HCID 70981091, compound → HCID 71003322, compound

HRID 1749082Notes

Reaction equation

HRID 1749082 reaction equation
C[O:2][C:3](=O)[C@@:4]([O:12][C:13]1[C:18]([N+:19]([O-])=O)=[CH:17][CH:16]=[C:15]([NH:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][C:25]=2[O:32][CH3:33])[N:14]=1)([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH3:5]>CC(O)=O.[Fe]>[CH3:33][O:32][C:25]1[CH:26]=[C:27]([O:30][CH3:31])[CH:28]=[CH:29][C:24]=1[CH2:23][NH:22][C:15]1[CH:16]=[CH:17][C:18]2[NH:19][C:3](=[O:2])[C@:4]([CH3:5])([C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)[O:12][C:13]=2[N:14]=1

Participants

4

Reactant 1

HCID 70981091HCID 70981091, compound

Product 1

HCID 71003322HCID 71003322, compoundYield 76.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

To (S)-2-[6-(2,4-dimethoxy-benzylamino)-3-nitro-pyridin-2-yloxy]-2-phenyl-propionic acid methyl ester (253 mg, 0.54 mmol) in AcOH (7 mL) was added Fe-powder (242 mg, 4.32 mmol). The mixture was heated at 60° C. for 3 hours and then allowed to cool. The mixture was evaporated in vacuo and then the residue was purified using SiO2 chromatography (1-1.5% MeOH/CH2Cl2) to give (S)-6-(2,4-dimethoxy-benzylamino)-3-methyl-3-phenyl-1H-pyrido[2,3-b][1,4]oxazin-2-one (167 mg) as a beige solid. MS: [M+H]+=406.

Workup

  1. temperatureto cool
  2. customThe mixture was evaporated in vacuo
  3. customthe residue was purified

Sources & evidence

ORD record
ord-5c43fbdf67af4671ab2bc4243eb64dee
Source dataset
uspto-grants-2015_10
Patent number
US09155743B2

Reaction notes

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