Hydrochloric Acid → 1-((2-(5-Bromo-3-(4-fluorophenoxy)pyridin-2-ylamino)thiazol-4-yl)methyl)piperazin-2-one

HRID 1806178Notes

Reaction equation

HRID 1806178 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:29][C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)[C:5]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH2:14][N:15]3[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][C:16]3=[O:28])[N:13]=2)=[N:6][CH:7]=1.Cl.O1CCOCC1>C(Cl)Cl.CCOCC>[Br:1][C:2]1[CH:3]=[C:4]([O:29][C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)[C:5]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH2:14][N:15]3[CH2:20][CH2:19][NH:18][CH2:17][C:16]3=[O:28])[N:13]=2)=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 57742856tert-Butyl 4-((2-(5-bromo-3-(4-fluorophenoxy)pyridin-2-ylamino)thiazol-4-yl)methyl)-3-oxopiperazine-1-carboxylate

Product 1

HCID 577428901-((2-(5-Bromo-3-(4-fluorophenoxy)pyridin-2-ylamino)thiazol-4-yl)methyl)piperazin-2-oneYield 73%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

In a 20 mL scintillation vial equipped with magnetic stirrer tert-butyl 4-((2-(5-bromo-3-(4-fluorophenoxy)pyridin-2-ylamino)thiazol-4-yl)methyl)-3-oxopiperazine-1-carboxylate (0.020 g, 0.035 mmol) was dissolved in 1 ml of CH2Cl2 and 4M HCl in dioxane (0.50 mL, 2.0 mmol) was added. The resulting mixture was agitated for 2 hours, diluted with 5 mL of ether and the solvent was decanted off. The residue was dried to provide the title compound (0.012 g, 73% yield). 1H NMR (d6-DMSO) δ 3.25-3.78 (m, 6H), 6.99 (s, 1H), 7.28-7.36 (m, 4H), 8.23 (s, 1H), 8.34 (s, 1H), 10.24 (s, 2H).

Workup

  1. customthe solvent was decanted off
  2. customThe residue was dried

Sources & evidence

ORD record
ord-1065d1c2e05c47478be9a4494653644f
Source dataset
uspto-grants-2013_01
Patent number
US08354540B2

Reaction notes

Loading…