Diethyl Ether → 6-[(1-Carbamoyl-1,2-dimethylpropyl)carbamoyl]furo[2,3-b]pyridine-5-carboxylic acid

HRID 365092Notes

Reaction equation

HRID 365092 reaction equation
[NH2:1][C:2]([CH3:9])([CH:6]([CH3:8])[CH3:7])[C:3]([NH2:5])=[O:4].[O:10]1[C:14]2=[N:15][C:16]3[C:22](=[O:23])[O:21][C:19](=[O:20])[C:17]=3[CH:18]=[C:13]2[CH:12]=[CH:11]1.CCOCC>O1CCCC1>[C:3]([C:2]([NH:1][C:22]([C:16]1[N:15]=[C:14]2[O:10][CH:11]=[CH:12][C:13]2=[CH:18][C:17]=1[C:19]([OH:21])=[O:20])=[O:23])([CH3:9])[CH:6]([CH3:8])[CH3:7])(=[O:4])[NH2:5]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 97937732-Amino-2,3-dimethylbutanamideHCID 13752513Furo[2,3-b]pryidine-5,6-Dicarboxylic anhydride

Product 1

HCID 137525146-[(1-Carbamoyl-1,2-dimethylpropyl)carbamoyl]furo[2,3-b]pyridine-5-carboxylic acidYield 97.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Amino-2,3-dimethylbutyramide (2.1 g, 0.016 mol) is added to a stirred suspension of furo[2,3-b]pyridine-5,6-dicarboxylic acid anhydride (3.0 g, 0.016 mol) in tetrahydrofuran (7.5 mL) and the mixture allowed to stir at room temperature for 16 hours. The reaction mixture is then stirred at 60° C. for one hour, cooled to room temperature, ether added, and the solid filtered off and dried to give 5 g of 6-[(1-carbamoyl-1,2-dimethylpropyl)carbamoyl]furo[2,3-b]pyridine-5-carboxylic acid mp 192°-196° C. (dec).

Workup

  1. stirringThe reaction mixture is then stirred at 60° C. for one hour
  2. temperaturecooled to room temperature
  3. filtrationthe solid filtered off
  4. customdried

Sources & evidence

ORD record
ord-883bbe10d0db45959646764428f3d2c5
Source dataset
uspto-grants-1986_08
Patent number
US04608079

Reaction notes

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