Formamide → HCID 22628457, compound

HRID 278492Notes

Reaction equation

C[O-].[Na+].[OH:4][CH2:5][CH:6]([N:20]1[CH:24]=[C:23]([C:25]([NH2:27])=[O:26])[N:22]=[CH:21]1)[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15](OCC)=[O:16])[CH:10]=1.O.C([NH2:31])=O>>[C:15]([C:11]1[CH:10]=[C:9]([CH2:8][CH2:7][CH:6]([N:20]2[CH:24]=[C:23]([C:25]([NH2:27])=[O:26])[N:22]=[CH:21]2)[CH2:5][OH:4])[CH:14]=[CH:13][CH:12]=1)(=[O:16])[NH2:31]

Participants

Reactant 4

HCID 713Formamide

HCID 962Water

HCID 10942334Sodium Methoxide

HCID 70097076HCID 70097076, compound

Product 1

HCID 22628457HCID 22628457, compoundYield 71.6%

Conditions

Temperature: 110 °C

Procedure

Sodium methoxide (39 mg, 0.72 mmol) was added to a stirred solution of 1-{1-hydroxy-4-[3-(ethoxycarbonyl)phenyl]-2-butyl}-imidazole-4-carboxamide (obtained in Example 10(1))(60 mg, 0.18 mmol) in formamide (1.5 ml), and the reaction mixture was stirred at 110° C. for 3 h. After cooling, the reaction mixture was poured into water (5 ml). The residue was purified by HP-20 (16 cc) column chromatography eluting with water/2-propanol (9:1) and lyophilized to give 1[4-(3-carbamoylphenyl)-1-hydroxy-2-butyl]imidazole-4-carboxamide (39.2 mg, 71.6%) as an amorphous solid.

Workup

temperatureAfter cooling
customThe residue was purified by HP-20 (16 cc) column chromatography
washeluting with water/2-propanol (9:1)

Sources & evidence

ORD record: ord-eb00d508d53944c98641eb8871074df4
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06359145B1

Reaction notes

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