tert-Butyl 4-(2-Bromoacetyl)piperidine-1-carboxylate → Tert-butyl 4-(2-(5-bromo-3-(4-fluorophenoxy)pyridin-2-ylamino)thiazol-4-yl)piperidine-1-carboxylate

HRID 335243Notes

Reaction equation

HRID 335243 reaction equation
C([NH:9][C:10]([NH:12][C:13]1[C:18]([O:19][C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)=[CH:17][C:16]([Br:27])=[CH:15][N:14]=1)=[S:11])(=O)C1C=CC=CC=1.Br[CH2:29][C:30]([CH:32]1[CH2:37][CH2:36][N:35]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:34][CH2:33]1)=O>C(O)C>[Br:27][C:16]1[CH:17]=[C:18]([O:19][C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[C:13]([NH:12][C:10]2[S:11][CH:29]=[C:30]([CH:32]3[CH2:37][CH2:36][N:35]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:34][CH2:33]3)[N:9]=2)=[N:14][CH:15]=1

Participants

4

Reactant 2

HCID 18187487tert-Butyl 4-(2-Bromoacetyl)piperidine-1-carboxylateHCID 866314841-Benzoyl-3-(5-bromo-3-(4-fluorophenoxy)pyridin-2-yl)thiourea

Product 1

HCID 86631531Tert-butyl 4-(2-(5-bromo-3-(4-fluorophenoxy)pyridin-2-ylamino)thiazol-4-yl)piperidine-1-carboxylateYield 74.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(5-bromo-3-(4-fluorophenoxy)pyridin-2-yl)thiourea (3.00 g, 8.77 mmol; prepared according to Example 179, Step D), TEA (2.08 mL, 14.9 mmol) and tert-butyl 4-(2-bromoacetyl)piperidine-1-carboxylate (3.49 g, 11.4 mmol) were refluxed in ethanol (75 mL) for 2 hours. The reaction was cooled to room temperature and filtered to afford the title compound (3.6 g, 74.7% yield).

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-a6ce5999e2e44d5aa16260468348c2f9
Source dataset
uspto-grants-2014_11
Patent number
US08883828B2

Reaction notes

Loading…