Hydrochloric Acid → Methyl 5-(4-isopropyl-4-methyl-5-oxo-2-imidazolidinyl)furo[3,2-b]pyridine-6-carboxylate

HRID 256123

Reaction equation

[CH:1]([C:4]1([CH3:23])[C:8](=[O:9])[NH:7][C:6]([C:10]2[N:15]=[C:14]3[CH:16]=[CH:17][O:18][C:13]3=[CH:12][C:11]=2[C:19]([O:21][CH3:22])=[O:20])=[N:5]1)([CH3:3])[CH3:2].Cl.C([BH3-])#N.[Na+].[OH-].[Na+]>CO.CN(C1C=CC(N=NC2C=CC(S(O)(=O)=O)=CC=2)=CC=1)C>[CH:1]([C:4]1([CH3:23])[C:8](=[O:9])[NH:7][CH:6]([C:10]2[N:15]=[C:14]3[CH:16]=[CH:17][O:18][C:13]3=[CH:12][C:11]=2[C:19]([O:21][CH3:22])=[O:20])[NH:5]1)([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 22.1 mmol of methyl 5-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)furo[3,2-b]pyridine-6-carboxylate in methanol is cooled to 0° C. and a few drops of methyl orange indicator added. The solution is stirred and treated with 22.1 mmol of concentrated hydrochloric acid. The solution is then treated with 22.1 mmol of sodium cyanoborohydride, and the pH maintained at ~3 by the addition of 2N methanolic HCl, stirred overnight, cooled to 0° C. and the pH of the solution adjusted to about 0 with HCl to decompose residual NaCNBH3. The pH is thereafter adjusted to 5-6 with 5N NaOH. The methanol is removed in vacuo and water added to dissolve inorganic salts. The mixture is extracted with CH2Cl2 and the extracts dried and concentrated to give the title compound.

Workup

stirringstirred overnight
customThe methanol is removed in vacuo and water
additionadded
dissolutionto dissolve inorganic salts
extractionThe mixture is extracted with CH2Cl2
customthe extracts dried
concentrationconcentrated

Sources & evidence

ORD record: ord-1339a0d0f72a414ebde117ac8075cb78
Source dataset: uspto-grants-1987_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04701208

Linked notes

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