1,1'-Carbonyldiimidazole → Tert-butyl 4-[5-(3-methyl-[1,2,4]-oxadiazol-5-yl)-thiazol-2-yl]piperazine-1-carboxylate

HRID 1594008Notes

Reaction equation

HRID 1594008 reaction equation
[C:1]([C:4]1[S:8][C:7]([N:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)=[N:6][CH:5]=1)([OH:3])=O.C1N=CN(C(N2C=NC=C2)=O)C=1.O[NH:35][C:36](=[NH:38])[CH3:37].ClCCCl.C(O)C>CN(C=O)C>[CH3:37][C:36]1[N:38]=[C:1]([C:4]2[S:8][C:7]([N:9]3[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]3)=[N:6][CH:5]=2)[O:3][N:35]=1

Participants

6

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 229016121,2-Dichloroethane ethanolHCID 672940122-{4-[(Tert-butoxy)carbonyl]piperazin-1-yl}-1,3-thiazole-5-carboxylic acidHCID 178465666HCID 178465666, compound

Product 1

HCID 69423493Tert-butyl 4-[5-(3-methyl-[1,2,4]-oxadiazol-5-yl)-thiazol-2-yl]piperazine-1-carboxylateYield 21%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

939 mg (3.0 mmol) of tert-butyl 4-(5-carboxythiazol-2-yl)piperazine-1-carboxylate [Precursor BBB61] were dissolved in DMF (15 ml) together with 534 mg (3.3 mmol) of CDI and the solution was stirred at RT 4 h. Subsequently, 243 mg (3.3 mmol) of N-hydroxyacetamidine were added and the mixture was stirred at 120° C. a further 4 h. The reaction solution was then poured onto water and the resulting precipitate was filtered off and washed with water. By means of CC (DCE/ethanol mixture) of the residue, 220 mg (0.63 mmol, 21%) of tert-butyl 4-[5-(3-methyl-[1,2,4]-oxadiazol-5-yl)-thiazol-2-yl]piperazine-1-carboxylate were obtained.

Workup

  1. stirringthe mixture was stirred at 120° C. a further 4 h
  2. additionThe reaction solution was then poured onto water
  3. filtrationthe resulting precipitate was filtered off
  4. washwashed with water

Sources & evidence

ORD record
ord-84ca0a66722546de8554c19860496988
Source dataset
uspto-grants-2007_11
Patent number
US07300939B2

Reaction notes

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