Ethyl Acetate → HCID 67255656, compound

HRID 1830719Notes

Reaction equation

HRID 1830719 reaction equation
[CH3:1][O:2][C:3](=[O:25])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([O:13]C2C=CC([N+]([O-])=O)=CC=2)=O)=[C:6]([O:23][CH3:24])[CH:5]=1.[CH3:26][C:27]1[N:28]=[CH:29][C:30]([NH2:33])=[N:31][CH:32]=1.CCOC(C)=O>CN1C(=O)CCC1>[CH3:1][O:2][C:3](=[O:25])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([NH:33][C:30]2[CH:29]=[N:28][C:27]([CH3:26])=[CH:32][N:31]=2)=[O:13])=[C:6]([O:23][CH3:24])[CH:5]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 3132155-Methylpyrazin-2-amineHCID 66906303HCID 66906303, compound

Product 1

HCID 67255656HCID 67255656, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a stirred solution of 3-methoxy-4-(4-nitro-phenoxycarbonylamino)-benzoic acid methyl ester (11.7 g, 33.8 mmol) in 34 mL NMP at room temperature under nitrogen was added 5-methyl-2-aminopyrazine (3.69 g, 33.8 mmol) and the reaction was immersed in an 85° C. oil bath. After 6 hours the reaction was allowed to cool to room temperature and a precipitate formed. EtOAc (200 mL) was added and the precipitate was isolated by filtration (4.7 g, 44%). 1H-NMR (400 MHz, d6-DMSO) 6 8.79 (br s, 1H), 8.36 (d, 1H), 8.23 (s, 1H), 7.60 (d, 1H), 7.52 (s, 1H), 3.98 (s, 3H), 3.81 (s, 3H), 2.42 (s, 3H).

Workup

  1. customwas immersed in an 85° C.
  2. customa precipitate formed
  3. customthe precipitate was isolated by filtration (4.7 g, 44%)

Sources & evidence

ORD record
ord-12649f61aa2f4ecfa7e37a17d506951f
Source dataset
uspto-grants-2006_06
Patent number
US07067506B2

Reaction notes

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