Diisopropylethylamine → Methyl 2-{4-[(tert-butoxycarbonyl)amino]piperidin-1-yl}-1,3-thiazole-5-carboxylate

HRID 2233898Notes

Reaction equation

HRID 2233898 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:3][CH2:2]1.Br[C:16]1[S:17][C:18]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][N:20]=1.C(N(C(C)C)CC)(C)C>CN(C=O)C>[C:10]([O:9][C:8]([NH:7][CH:4]1[CH2:3][CH2:2][N:1]([C:16]2[S:17][C:18]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][N:20]=2)[CH2:6][CH2:5]1)=[O:14])([CH3:11])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 7238334-(N-Boc-amino)piperidineHCID 2773502Methyl 2-bromothiazole-5-carboxylate

Product 1

HCID 59679281Methyl 2-{4-[(tert-butoxycarbonyl)amino]piperidin-1-yl}-1,3-thiazole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

tert-Butyl piperidin-4-ylcarbamate (4.5 g, 22 mmol), methyl 2-bromo-1,3-thiazole-5-carboxylate (5.0 g, 22 mmol), and diisopropylethylamine (3.8 ml, 22 mmol) were suspended in anhydrous DMF and heated to an external temperature of 130° C. for 1.5 hours. The DMF was removed and the solid was partitioned with EtOAc and water. The combined organic extracts were washed with brine, dried with MgSO4 and concentrated to a yellow solid (7.05 g, 94%).

Workup

  1. customThe DMF was removed
  2. customthe solid was partitioned with EtOAc and water
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated to a yellow solid (7.05 g, 94%)

Sources & evidence

ORD record
ord-0e670a2c090c46fc9d6661a58f2d55df
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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