Acetic Acid → Tert-butyl 2-{[4-({[2-(acetylamino)-1,3-thiazol-4-yl]methyl}amino)benzoyl]carbamoyl}hydrazinecarboxylate

HRID 1892528Notes

Reaction equation

HRID 1892528 reaction equation
[C:1]([NH:4][C:5]1[S:6][CH:7]=[C:8]([CH:10]=[N:11][C:12]2[CH:31]=[CH:30][C:15]([C:16]([NH:18][C:19]([NH:21][NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[O:20])=[O:17])=[CH:14][CH:13]=2)[N:9]=1)(=[O:3])[CH3:2].[BH4-].[Na+].C(O)(=O)C>O1CCCC1.CO>[C:1]([NH:4][C:5]1[S:6][CH:7]=[C:8]([CH2:10][NH:11][C:12]2[CH:13]=[CH:14][C:15]([C:16]([NH:18][C:19]([NH:21][NH:22][C:23]([O:25][C:26]([CH3:28])([CH3:27])[CH3:29])=[O:24])=[O:20])=[O:17])=[CH:30][CH:31]=2)[N:9]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 86650032Tert-butyl 2-{[4-({[2-(acetylamino)-1,3-thiazol-4-yl]methylidene}amino)benzoyl]carbamoyl}hydrazinecarboxylate

Product 1

HCID 86650033Tert-butyl 2-{[4-({[2-(acetylamino)-1,3-thiazol-4-yl]methyl}amino)benzoyl]carbamoyl}hydrazinecarboxylateYield 83.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

tert-Butyl 2-{[4-({[2-(acetylamino)-1,3-thiazol-4-yl]methylidene}amino)benzoyl]carbamoyl}hydrazinecarboxylate (778.5 mg, 1.800 mmol) was dissolved in a mixed solvent of anhydrous tetrahydrofuran (18 ml) and anhydrous methanol (9 ml), and the mixture was cooled to 0° C. Sodium borohydride (68.1 mg, 1.80 mmol) was added and the mixture was stirred at room temperature for 30 min. Acetic acid (0.22 ml, 3.85 mmol) was added and the mixture was stirred for 15 min and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. BW-300SP 40 g, dichloromethane:methanol=20:1→15:1). The pure fractions were concentrated under reduced pressure, ethyl acetate (30 ml) and tert-butyl methyl ether (10 ml) were added to the residue, and the resulting solid was collected by filtration and dried under reduced pressure to give tert-butyl 2-{[4-({[2-(acetylamino)-1,3-thiazol-4-yl]methyl}amino)benzoyl]carbamoyl}hydrazinecarboxylate (653.1 mg, 1.503 mmol, yield 83.5%) as a white solid.

Workup

  1. stirringthe mixture was stirred for 15 min
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. BW-300SP 40 g, dichloromethane:methanol=20:1→15:1)
  4. concentrationThe pure fractions were concentrated under reduced pressure, ethyl acetate (30 ml) and tert-butyl methyl ether (10 ml)
  5. additionwere added to the residue
  6. filtrationthe resulting solid was collected by filtration
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-9b45fb9e6bc24f5aada1644d06f6e43f
Source dataset
uspto-grants-2013_08
Patent number
US08507690B2

Reaction notes

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