Sodium borohydride → HCID 131725161, compound

HRID 497064Notes

Reaction equation

HRID 497064 reaction equation
CO.C(Cl)(Cl)[Cl:4].[NH2:7][C:8]1[S:9][CH:10]=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20]([CH2:22][N:23]([C:34]3[CH:42]=[CH:41][C:37]4[N:38]=[CH:39][S:40][C:36]=4[CH:35]=3)[C:24]([CH2:26][CH:27]3[CH2:32][CH2:31][C:30](=[O:33])[CH2:29][CH2:28]3)=[O:25])=[O:21])=[CH:15][CH:14]=2)[N:12]=1.[BH4-].[Na+]>O>[ClH:4].[NH2:7][C:8]1[S:9][CH:10]=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20]([CH2:22][N:23]([C:34]3[CH:42]=[CH:41][C:37]4[N:38]=[CH:39][S:40][C:36]=4[CH:35]=3)[C:24]([CH2:26][CH:27]3[CH2:32][CH2:31][CH:30]([OH:33])[CH2:29][CH2:28]3)=[O:25])=[O:21])=[CH:15][CH:14]=2)[N:12]=1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 21584188Chloroform methanolHCID 131725163HCID 131725163, compound

Product 1

HCID 131725161HCID 131725161, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A methanol-chloroform (40 ml-20 ml) solution of N-({[4-(2-aminothiazol-4-yl)phenyl]carbamoyl}methyl)-N-benzothiazol-6-yl-4-oxocyclohexanecarboxyamide (430 mg) was mixed with sodium borohydride (0.19 g) at 0° C. and then stirred at room temperature for 1 hour. The reaction solution was mixed with water and extracted with chloroform, the organic layer was dried with anhydrous sodium sulfate and filtered, and then the solvent was evaporated under a reduced pressure. The thus obtained crude product was purified by SCG (chloroform/methanol/27% aqueous ammonia=94.8/5/0.2). This was dissolved in chloroform-methanol (10 ml-10 ml) and mixed with 4 M hydrogen chloride in ethyl acetate (1 ml), and then the solvent was evaporated under a reduced pressure. By recrystallizing the thus obtained crude crystals from isopropyl alcohol-ethyl acetate (3/1), 259 mg of N-({[4-(2-aminothiazol-4-yl)phenyl]carbamoyl}methyl)-N-benzothiazol-6-yl-4-hydroxycyclohexanecarboxyamide monohydrochloride (pale yellow crystals) was obtained.

Workup

  1. extractionextracted with chloroform
  2. dry with materialthe organic layer was dried with anhydrous sodium sulfate
  3. filtrationfiltered
  4. customthe solvent was evaporated under a reduced pressure
  5. customThe thus obtained crude product
  6. customwas purified by SCG (chloroform/methanol/27% aqueous ammonia=94.8/5/0.2)
  7. dissolutionThis was dissolved in chloroform-methanol (10 ml-10 ml)
  8. additionmixed with 4 M hydrogen chloride in ethyl acetate (1 ml)
  9. customthe solvent was evaporated under a reduced pressure
  10. customBy recrystallizing the
  11. customthus obtained crude crystals from isopropyl alcohol-ethyl acetate (3/1)

Sources & evidence

ORD record
ord-50c04f7cd5064d6ba07541bf8ca56a90
Source dataset
uspto-grants-2005_09
Patent number
US06949543B2

Reaction notes

Loading…