Triethylamine → HCID 58459770, compound

HRID 1675346Notes

Reaction equation

HRID 1675346 reaction equation
[CH2:1]1[C:5]2[CH2:6][NH:7][CH2:8][C:4]=2[CH2:3][N:2]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].Br[C:17]1[S:18][C:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:20][N:21]=1.C(N(CC)CC)C>CN(C=O)C>[CH2:25]([O:24][C:22]([C:19]1[S:18][C:17]([N:7]2[CH2:6][C:5]3[CH2:1][N:2]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3][C:4]=3[CH2:8]2)=[N:21][CH:20]=1)=[O:23])[CH3:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3614103Ethyl 2-bromothiazole-5-carboxylateHCID 45792434HCID 45792434, compound

Product 1

HCID 58459770HCID 58459770, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

tert-Butyl 3,4,5,6-tetrahydro-1H-pyrrolo[3,4-c]pyrrole-2-carboxylate (1.2 g, 5.7 mmol), ethyl 2-bromothiazole-5-carboxylate (1.69 g, 7.17 mmol) and triethylamine (1.09 ml, 7.84 mmol) were stirred at 100° C. in 70 ml of DMF for 7 h. The residue was filtered off, the filtrate was concentrated and the remaining residue was extracted with ethyl acetate. 1.34 g of crude product were obtained, which were reacted without further purification (M+H+: 366.14).

Workup

  1. filtrationThe residue was filtered off
  2. concentrationthe filtrate was concentrated
  3. extractionthe remaining residue was extracted with ethyl acetate

Sources & evidence

ORD record
ord-2b1223d512084bd68406192258912501
Source dataset
uspto-grants-2011_08
Patent number
US08003677B2

Reaction notes

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