Ethanol → HCID 178441636, compound

HRID 2233883Notes

Reaction equation

[C:1]([C:3]1C=[C:5]([C:9](OCC)=O)[NH:6][C:7]=1[CH3:8])#[N:2].[C:14](OCC)(=O)[CH2:15][C:16](C)=O.[Na].CC[OH:26]>>[CH2:9]([C:5]1[N:2]=[C:1]([OH:26])[CH:3]=[C:7]([CH3:8])[N:6]=1)[CH2:14][CH2:15][CH3:16]

Participants

Reactant 4

HCID 702Ethanol

HCID 8868Ethyl Acetoacetate

HCID 5360545Sodium

HCID 58066127Ethyl 4-cyano-5-methyl-1H-pyrrole-2-carboxylate

Product 1

HCID 178441636HCID 178441636, compound

Procedure

Pentanimidamide hydrochloride (3.2 g) (prepared according to Garigipati, R. S.; Tetrahedron Lett 1990, 31 (14), 1969) was treated with ethyl acetoacetate (3.05 g) in a modified procedure using sodium (1.62 g) in anhydrous EtOH (50 ml) as base (as described in Salimbeni, Aldo; et al. J. Med. Chem. (1995), 38(24), 4806-20) affording the title compound (4.04 g).

Sources & evidence

ORD record: ord-97e4c189db174a7db8893f763dd025bc
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07709503B2

Reaction notes

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