Hydrochloric Acid → HCID 59313682, compound

HRID 218311Notes

Reaction equation

HRID 218311 reaction equation
[NH2:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]([NH2:9])=[O:8].[C:10]12[C:18](=[O:19])[O:17][C:15](=[O:16])[C:11]=1[CH2:12][CH2:13][CH2:14]2.Cl>C1COCC1>[C:7]([C:3]1[N:2]([NH:1][C:18]([C:10]2[CH2:14][CH2:13][CH2:12][C:11]=2[C:15]([OH:17])=[O:16])=[O:19])[CH:6]=[CH:5][CH:4]=1)(=[O:8])[NH2:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3248541H,3H,4H,5H,6H-cyclopenta(c)furan-1,3-dioneHCID 104191801-Amino-1H-pyrrole-2-carboxamide

Product 1

HCID 59313682HCID 59313682, compoundYield 92.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-Amino-1H-pyrrole-2-carboxamide (91 mg, 0.724 mmol) was dissolved in THF (3 mL), then 1-cyclopentene-1,2-dicarboxylic anhydride (100 mg, 0.724 mmol) was added. The reaction was stirred at rt for 30 min, then 0.5 M HCl (10 mL) was added. The precipitated product was filtered, rinsing with more 0.5 M HCl. The solids were dried to give 19A (177 mg, 92%). 19A had an analytical HPLC retention time=1.597 min (Phenomenex Luna 4.6×50 mm, 10-90% aqueous MeOH over 5 min containing 0.1% TFA) and a LC/MS M++1=264.

Workup

  1. filtrationThe precipitated product was filtered
  2. washrinsing with more 0.5 M HCl
  3. customThe solids were dried

Sources & evidence

ORD record
ord-af422c0d386349b9bd227976407eb246
Source dataset
uspto-grants-2012_06
Patent number
US08198438B2

Reaction notes

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