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

HRID 580297Notes

Reaction equation

HRID 580297 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>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

4

Reactant 2

HCID 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, either 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. additionadded
  4. filtrationthe solid filtered off
  5. customdried

Sources & evidence

ORD record
ord-7535937d28fd4c95929950089c44a72c
Source dataset
uspto-grants-1988_06
Patent number
US04752323

Reaction notes

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