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

HRID 1892474Notes

Reaction equation

HRID 1892474 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12]2[N:13]=[C:14]([NH:17][C:18](=[O:20])[CH3:19])[S:15][CH:16]=2)=[CH:6][CH:5]=1.[C:21]([N:28]1C=CN=C1)(N1C=CN=C1)=[O:22].[C:33]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])(=[O:36])[NH:34]N>O1CCCC1>[NH:28]([C:21]([O:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12]2[N:13]=[C:14]([NH:17][C:18](=[O:20])[CH3:19])[S:15][CH:16]=2)=[CH:6][CH:5]=1)=[O:22])[NH:34][C:33]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 70091tert-Butyl carbazate3×HCID 86227320N-(4-{2-[4-(2-Hydroxyethyl)phenyl]ethyl}thiazol-2-yl)acetamide

Product 1

HCID 866499832-(4-{2-[2-(Acetylamino)-1,3-thiazol-4-yl]ethyl}phenyl)ethyl tert-butyl hydrazine-1,2-dicarboxylateYield 93.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

To a suspension of N-(4-{2-[4-(2-hydroxyethyl)phenyl]ethyl}-1,3-thiazol-2-yl)acetamide (552.5 mg, 1.799 mmol) in anhydrous tetrahydrofuran (8 ml) was added 1,1′-carbonyldiimidazole (437.8 mg, 2.700 mmol), and the mixture was stirred at 45° C. for 0.5 hr. tert-Butyl carbazate (356.8 mg, 2.700 mmol) was added. After stirring for 1 hr, tert-butyl carbazate (356.6 mg, 2.698 mmol) was added. After stirring for 3 hr, tert-butyl carbazate (357.0 mg, 2.701 mmol) was further added. After stirring for 24 hr, the mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. DM1025 60 g, ethyl acetate:hexane=5:5→7:3). The residue was further purified by silica gel column chromatography (Sep pak-5 g, ethyl acetate:hexane=7:3) to give 2-(4-{2-[2-(acetylamino)-1,3-thiazol-4-yl]ethyl}phenyl)ethyl tert-butyl hydrazine-1,2-dicarboxylate (755.9 mg, 1.685 mmol, yield 93.6%) as white crystals.

Workup

  1. stirringAfter stirring for 1 hr
  2. stirringAfter stirring for 3 hr
  3. stirringAfter stirring for 24 hr
  4. concentrationthe mixture was concentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. DM1025 60 g, ethyl acetate:hexane=5:5→7:3)
  6. customThe residue was further purified by silica gel column chromatography (Sep pak-5 g, ethyl acetate:hexane=7:3)

Sources & evidence

ORD record
ord-9421a9102c9947efbdcbed0acbd9e6d7
Source dataset
uspto-grants-2013_08
Patent number
US08507690B2

Reaction notes

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