Triethylamine → Tert-butyl 2-({4-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}methyl)hydrazinecarboxylate

HRID 1257408Notes

Reaction equation

HRID 1257408 reaction equation
Cl[CH2:2][C:3]1[S:4][CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[N:7]=1.[NH:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[NH2:19].C(N(CC)CC)C>CN(C)C=O.C(OCC)(=O)C.O>[F:15][C:14]([F:17])([F:16])[C:10]1[CH:9]=[C:8]([C:6]2[N:7]=[C:3]([CH2:2][NH:19][NH:18][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[S:4][CH:5]=2)[CH:13]=[CH:12][CH:11]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 70091tert-Butyl carbazateHCID 629239612-(Chloromethyl)-4-[3-(trifluoromethyl)phenyl]-1,3-thiazole

Product 1

HCID 66939173Tert-butyl 2-({4-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}methyl)hydrazinecarboxylateYield 66.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The compound (0.60 g) obtained in Example 103b was dissolved in N,N-dimethylformamide (3 mL), and tert-butyl hydrazinecarboxylate (1.45 g) and triethylamine (0.61 mL) were added. The reaction mixture was stirred at room temperature for 96 hr, and diluted with ethyl acetate and water. The ethyl acetate layer was separated, washed with saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (carrier: silica gel, eluent: hexane-ethyl acetate) to give tert-butyl 2-({4-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}methyl)hydrazinecarboxylate (0.54 g) as a colorless solid. The solid was dissolved in 10% hydrogen chloride-ethanol (30 mL), and the mixture was stirred at room temperature for 16 hr. The reaction mixture was concentrated under reduced pressure, and the residue was washed with diisopropyl ether to give the title compound (0.45 g) as colorless crystals.

Workup

  1. customThe ethyl acetate layer was separated
  2. washwashed with saturated brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography (carrier: silica gel, eluent: hexane-ethyl acetate)

Sources & evidence

ORD record
ord-c6c7fc9ac25f4ffaad6ce45710317889
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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