1,1'-Carbonyldiimidazole → 4-{2-[2-(Acetylamino)-1,3-thiazol-4-yl]ethyl}phenyl tert-butyl hydrazine-1,2-dicarboxylate

HRID 1892470Notes

Reaction equation

HRID 1892470 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[N:11]=[C:12]([NH:15][C:16](=[O:18])[CH3:17])[S:13][CH:14]=2)=[CH:4][CH:3]=1.[C:19]([N:26]1C=CN=C1)(N1C=CN=C1)=[O:20].[C:31]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])(=[O:34])[NH:32]N>O1CCCC1>[NH:26]([C:19]([O:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[N:11]=[C:12]([NH:15][C:16](=[O:18])[CH3:17])[S:13][CH:14]=2)=[CH:4][CH:3]=1)=[O:20])[NH:32][C:31]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 70091tert-Butyl carbazateHCID 86649977N-{4-[2-(4-hydroxyphenyl)ethyl]-1,3-thiazol-2-yl}acetamide

Product 1

HCID 866499784-{2-[2-(Acetylamino)-1,3-thiazol-4-yl]ethyl}phenyl tert-butyl hydrazine-1,2-dicarboxylateYield 50.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of N-{4-[2-(4-hydroxyphenyl)ethyl]-1,3-thiazol-2-yl}acetamide (655.8 mg, 2.50 mmol) in anhydrous tetrahydrofuran (12 ml) was added 1,1′-carbonyldiimidazole (608.1 mg, 3.75 mmol). After stirring at 45° C. for 1 hr, the mixture was cooled to room temperature. tert-Butyl carbazate (495.6 mg, 3.75 mmol) was added, and the mixture was stirred at room temperature for 15 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. BW-300SP 80 g, ethyl acetate:hexane=1:1→3:2) and chemically modified silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. DM-2035 45 g, dichloromethane:methanol=50:1→20:1) to give 4-{2-[2-(acetylamino)-1,3-thiazol-4-yl]ethyl}phenyl tert-butyl hydrazine-1,2-dicarboxylate (526.4 mg, 1.252 mmol, yield 50.0%) as a white solid.

Workup

  1. temperaturethe mixture was cooled to room temperature
  2. stirringthe mixture was stirred at room temperature for 15 hr
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. BW-300SP 80 g, ethyl acetate:hexane=1:1→3:2) and chemically modified silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. DM-2035 45 g, dichloromethane:methanol=50:1→20:1)

Sources & evidence

ORD record
ord-3a66605e2c9245dabcf0c70e190a4e5d
Source dataset
uspto-grants-2013_08
Patent number
US08507690B2

Reaction notes

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