Hydrochloric Acid → HCID 178444769, compound

HRID 1194317Notes

Reaction equation

HRID 1194317 reaction equation
[NH:1]([C:5]1[S:6][CH:7]=[C:8]([C:10]2[O:11][C:12]([C:15](=O)[N:16]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH3:17])=[CH:13][CH:14]=2)[N:9]=1)[C:2]([NH2:4])=[NH:3].B#B.Cl.[OH-].[Na+]>O1CCCC1>[NH:1]([C:5]1[S:6][CH:7]=[C:8]([C:10]2[O:11][C:12]([CH2:15][N:16]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH3:17])=[CH:13][CH:14]=2)[N:9]=1)[C:2]([NH2:4])=[NH:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 6328200DiboronHCID 178444803HCID 178444803, compound

Product 1

HCID 178444769HCID 178444769, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Guanidino-4-(5-[N-n-hexyl-N-methylcarbamoyl]-2-furyl)thiazole (2.0 g., 4 mmole) was reduced with an excess of diborane in tetrahydrofuran substantially according to the procedure of Example 1. At the end of the reduction, 15 ml. of 6N hydrochloric acid was added and the resulting mixture was heated under reflux for 25 minutes. The cooled mixture was then made alkaline with 10N sodium hydroxide solution and the solid which precipitated was removed by filtration. The remaining aqueous phase was extracted with n-butanol, and the extracts were dried (Na2SO4) and evaporated. The residue was purified by column chromatography on silica gel using 1:5 methanolchloroform as eluant, giving two crops of the title compound, 300 mg. and 460 mg.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 25 minutes
  3. customthe solid which precipitated
  4. customwas removed by filtration
  5. extractionThe remaining aqueous phase was extracted with n-butanol
  6. dry with materialthe extracts were dried (Na2SO4)
  7. customevaporated
  8. customThe residue was purified by column chromatography on silica gel using 1:5 methanolchloroform as eluant

Sources & evidence

ORD record
ord-c0f5434ba8d5454c943053b9bd11f343
Source dataset
uspto-grants-1989_03
Patent number
US04814341

Reaction notes

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