Diethyl Ether → 6-(4-Isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)furo[2,3-b]pyridine-5-carboxylic acid

HRID 1906113Notes

Reaction equation

HRID 1906113 reaction equation
[O:1]1[C:5]2=[N:6][C:7]3[C:13](=O)[O:12][C:10](=[O:11])[C:8]=3[CH:9]=[C:4]2[CH:3]=[CH:2]1.[NH2:15][C:16]([CH3:23])([CH:20]([CH3:22])[CH3:21])[C:17]([NH2:19])=[O:18].CCOCC>C1COCC1>[CH:20]([C:16]1([CH3:23])[C:17](=[O:18])[NH:19][C:13]([C:7]2[N:6]=[C:5]3[O:1][CH:2]=[CH:3][C:4]3=[CH:9][C:8]=2[C:10]([OH:12])=[O:11])=[N:15]1)([CH3:22])[CH3:21]

Participants

5

Reactant 3

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

Product 1

HCID 137524676-(4-Isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)furo[2,3-b]pyridine-5-carboxylic acidYield 27%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Furo[2,3-b]pyridine-5,6-Dicarboxylic anhydride (2.50 g, 0.013 mol) is suspended in 40 mLs anhydrous THF and (+)-2-amino-2,3-dimethylbutyramide (1.72 g, 0.013 mol) is added. The mixture is stirred under N2 at room temperature for 16 hours. The solution is poured into 150 mLs anhydrous ether, and the resulting solid is collected in 88.6% crude yield. The unpurified adduct is converted to the indicated product in the manner described in Example 38 for the racemic mixture. The (+)-isomer is recrystallized from absolute ethanol, and is isolated in 27.0% yield from the adduct., mp 244°-245° C. [α]D25 =44.5°.

Workup

  1. customthe resulting solid is collected in 88.6% crude yield
  2. customThe (+)-isomer is recrystallized from absolute ethanol
  3. customis isolated in 27.0% yield from the adduct
  4. custommp 244°-245° C. [α]D25 =44.5°

Sources & evidence

ORD record
ord-590526d4cdd649d1afe2d7c4507d7ea2
Source dataset
uspto-grants-1987_03
Patent number
US04650514

Reaction notes

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