Nitrogen → 5-{2-Amino-4-[2-(3,4,5-trihydroxy-phenyl)-acetylamino]-phenyl}-2-methyl-furan-3-carboxylic acid

HRID 383597Notes

Reaction equation

HRID 383597 reaction equation
N#N.[CH3:3][C:4]1[O:5][C:6]([C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:30])[CH2:20][C:21]3[CH:26]=[C:25]([OH:27])[C:24]([OH:28])=[C:23]([OH:29])[CH:22]=3)=[CH:14][C:13]=2[N+:31]([O-])=O)=[CH:7][C:8]=1[C:9]([OH:11])=[O:10]>CO.[Pd]>[NH2:31][C:13]1[CH:14]=[C:15]([NH:18][C:19](=[O:30])[CH2:20][C:21]2[CH:22]=[C:23]([OH:29])[C:24]([OH:28])=[C:25]([OH:27])[CH:26]=2)[CH:16]=[CH:17][C:12]=1[C:6]1[O:5][C:4]([CH3:3])=[C:8]([C:9]([OH:11])=[O:10])[CH:7]=1

Participants

5

Reactant 2

HCID 947NitrogenHCID 598198872-Methyl-5-{2-nitro-4-[2-(3,4,5-trihydroxy-phenyl)-acetylamino]-phenyl}-furan-3-carboxylic acid

Product 1

HCID 598198685-{2-Amino-4-[2-(3,4,5-trihydroxy-phenyl)-acetylamino]-phenyl}-2-methyl-furan-3-carboxylic acidYield 23.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

(The following reaction is done in an N2 atmosphere.) Dissolve 2-Methyl-5-{2-nitro-4-[2-(3,4,5-trihydroxy-phenyl)-acetylamino]-phenyl}-furan-3-carboxylic acid (61) (21 mg, 0.05 mmol) in MeOH (1.5 mL) and add Pd on carbon (10% (w/w) Pd content, 11.5 mg, 0.005 mmol) followed by NH4CO2H (68 mg, 1.08 mmol) at rt. Degas the reaction mixture carefully (flush with N2) and stir it for 17 h at rt. Filtrate reaction mixture through a short pad of celite and remove solvent. Purify the crude product by preparative RP HPLC (gradient, water/CH3CN 95:5 to 5:95) to obtain 5-{2-Amino-4-[2-(3,4,5-trihydroxy-phenyl)-acetylamino]phenyl}-2-methyl-furan-3-carboxylic acid (62) (4.6 mg, 23%) as a white solid. 1H NMR (400 MHz, CD3OD): 2.69 (s, 3H); 3.50 (s, 2H); 6.39 (s, 2H); 6.91 (s, 1H); 7.13 (br.d, 1H, J=8.6 Hz); 7.57 (d, 1H, J=8.6 Hz) 7.65 (br.s, 1H).

Workup

  1. custom(The following reaction
  2. customfollowed by NH4CO2H (68 mg, 1.08 mmol) at rt
  3. customDegas
  4. customthe reaction mixture carefully (flush with N2)
  5. customFiltrate reaction mixture through a short pad of celite
  6. customremove solvent
  7. customPurify the crude product by preparative RP HPLC (gradient, water/CH3CN 95:5 to 5:95)

Sources & evidence

ORD record
ord-9575ff54e84b40e189256baec91ced4c
Source dataset
uspto-grants-2013_02
Patent number
US08367677B2

Reaction notes

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