Hydrochloric Acid → HCID 178444826, compound

HRID 1194318Notes

Reaction equation

HRID 1194318 reaction equation
[CH2:1]([NH:7][C:8](=[NH:25])[NH:9][C:10]1[S:11][CH:12]=[C:13]([C:15]2[O:16][C:17]([C:20](=O)[N:21]([CH3:23])[CH3:22])=[CH:18][CH:19]=2)[N:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].B#B.Cl>O1CCCC1>[CH2:1]([NH:7][C:8](=[NH:25])[NH:9][C:10]1[S:11][CH:12]=[C:13]([C:15]2[O:16][C:17]([CH2:20][N:21]([CH3:22])[CH3:23])=[CH:18][CH:19]=2)[N:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6328200DiboronHCID 178444827HCID 178444827, compound

Product 1

HCID 178444826HCID 178444826, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(3-n-Hexylguanidino)-4-(5-[N,N-dimethylcarbamoyl]-2-furyl)thiazole (1.77 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, 20 ml. of 6N hydrochloric acid was added dropwise, very slowly, and then the mixture was heated at ca 90° C. to removed the majority of the tetrahydrofuran. The aqueous residue was made alkaline with 10N sodium hydroxide solution and then it was extracted with n-butanol. The dried (Na2SO4) extracts were evaporated in vacuo to give a dark-colored oil which was purified by chromatography on silica gel using 1:10 methanol-chloroform. This afforded the title compound, 950 mg, as an oil.

Workup

  1. temperaturevery slowly, and then the mixture was heated at ca 90° C.
  2. customto removed the majority of the tetrahydrofuran
  3. extractionit was extracted with n-butanol
  4. dry with materialThe dried (Na2SO4) extracts
  5. customwere evaporated in vacuo
  6. customto give a dark-colored oil which
  7. customwas purified by chromatography on silica gel using 1:10 methanol-chloroform

Sources & evidence

ORD record
ord-d01e254cb842417d99a0326b023927c8
Source dataset
uspto-grants-1989_03
Patent number
US04814341

Reaction notes

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