Pyrrolidine → N-(5-methyl-1,3-thiazol-2-yl)pyrrolidine-1-carboxamide

HRID 390702Notes

Reaction equation

HRID 390702 reaction equation
[CH3:1][C:2]1[S:6][C:5]([NH2:7])=[N:4][CH:3]=1.C1N=CN([C:13]([N:15]2[CH:19]=N[CH:17]=[CH:16]2)=[O:14])C=1.N1CCC[CH2:21]1>CN(C)C1C=CN=CC=1.O1CCCC1>[CH3:1][C:2]1[S:6][C:5]([NH:7][C:13]([N:15]2[CH2:16][CH2:17][CH2:21][CH2:19]2)=[O:14])=[N:4][CH:3]=1

Participants

6

Reactant 3

HCID 31268PyrrolidineHCID 682631,1'-CarbonyldiimidazoleHCID 3517702-Amino-5-methylthiazole

Product 1

HCID 47197229N-(5-methyl-1,3-thiazol-2-yl)pyrrolidine-1-carboxamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-methylthiazol-2-amine (4.8 g, 42 mmol), N,N-carbonyldiimidazole (9.8 g, 61 mmol), and 4-dimethylaminopyridine (0.1 g, 1.0 mmol) in tetrahydrofuran (90 mL) was heated at 65° C. for 6 hours. Pyrrolidine (5.1 mL, 61 mmol) was then added and heating was continued at 65° C. for 48 hours. The mixture was concentrated, and the residue was diluted with methanol and then triturated with diethyl ether. The solids were collected by filtration, washed with diethyl ether, and recrystallized from ethyl acetate to give the title compound.

Workup

  1. temperatureheating
  2. concentrationThe mixture was concentrated
  3. additionthe residue was diluted with methanol
  4. customtriturated with diethyl ether
  5. filtrationThe solids were collected by filtration
  6. washwashed with diethyl ether
  7. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-e7cbf7636c64439a8eafa7d98b00f189
Source dataset
uspto-grants-2013_02
Patent number
US08383657B2

Reaction notes

Loading…