Hydrochloric Acid → HCID 178512758, compound

HRID 1434693Notes

Reaction equation

HRID 1434693 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH:6][S:7]([C:10]1[CH:28]=[CH:27][C:13]([C:14]([NH:16][N:17]=[CH:18][C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([Cl:26])[CH:20]=2)=[NH:15])=[CH:12][CH:11]=1)(=[O:9])=[O:8].[BH3-]C#N.[Na+].Cl>C1COCC1>[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH:6][S:7]([C:10]1[CH:11]=[CH:12][C:13]([C:14]([NH:16][NH:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([Cl:26])[CH:20]=2)=[NH:15])=[CH:27][CH:28]=1)(=[O:9])=[O:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5003444Sodium cyanoborohydrideHCID 178512757HCID 178512757, compound

Product 1

HCID 178512758HCID 178512758, compoundYield 23.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-(thiazol-2-ylsulfamoyl)-N-(3,4-dichloro-benzylideneamino)-benzamidine (0.387 mmol) and NaCNBH3 (large excess) was stirred in THF (5 mL) at room temperature. To the solution was added 6 N HCl drop wise until all starting material is consumed. The solution was quenched with sat NaHCO3 and extracted with ethyl acetate. The organic phase was collected and concentrated in vacuo. The crude product was purification by reverse phase chromatography to yield 4-(thiazol-2-ylsulfamoyl)-N-(3,4-dichlorobenzylamino)-benzamidine (0.09 mmol).

Workup

  1. customis consumed
  2. customThe solution was quenched with sat NaHCO3
  3. extractionextracted with ethyl acetate
  4. customThe organic phase was collected
  5. concentrationconcentrated in vacuo
  6. custompurification by reverse phase chromatography

Sources & evidence

ORD record
ord-79dd3fddefec4826a7aaa60bd4da24b4
Source dataset
uspto-grants-2009_11
Patent number
US07615569B2

Reaction notes

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