4-Nitroanthranilic acid → HCID 22175043, compound

HRID 2221028Notes

Reaction equation

HRID 2221028 reaction equation
F[CH:2]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)[CH2:3][NH2:4].[N+:13]([C:16]1[CH:17]=[C:18]([NH2:25])[C:19](=[CH:23][CH:24]=1)[C:20](O)=[O:21])([O-:15])=[O:14].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[F:43][P-](F)(F)(F)(F)F>>[NH2:25][C:18]1[CH:17]=[C:16]([N+:13]([O-:15])=[O:14])[CH:24]=[CH:23][C:19]=1[C:20]([NH:4][CH2:3][CH2:2][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:6]=1[F:43])=[O:21]

Participants

4

Reactant 3

HCID 120764-Nitroanthranilic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68594232HCID 68594232, compound2×

Product 1

HCID 22175043HCID 22175043, compound

Procedure

2-Fluoro-4-methoxyphenylethylamine ((a): 1 equivalent), 4-nitroanthranilic acid ((b): 1 equivalent), HBTU (1.5 equivalents), and dry THF (0.5 M in (a)) were added to a dry round bottom flask. The mixture was allowed to stir for 10 hours at room temperature. The reaction was then dry loaded onto silica gel and purified via flash chromatography using hexanes/ethyl acetate. The pure fractions were combined and concentrated in vacuo to yield the product ((c): 2-amino-N-[2-(2-fluoro-4-methoxy-phenyl)-ethyl]-4-nitro-benzamide) as a pure solid.

Workup

  1. customThe reaction was then dry
  2. custompurified via flash chromatography
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c0c4cd9dd3e143a98b5fd114ee9a8cc0
Source dataset
uspto-grants-2008_05
Patent number
US07368453B2

Reaction notes

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