Hydrochloric Acid → HCID 57742597, compound

HRID 911904Notes

Reaction equation

HRID 911904 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:5]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH2:14][CH:15]3[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[C:16]3=[O:27])[N:13]=2)=[N:6][CH:7]=1.Cl>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([O:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:5]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH2:14][CH:15]3[CH2:19][CH2:18][NH:17][C:16]3=[O:27])[N:13]=2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86631526HCID 86631526, compound

Product 1

HCID 57742597HCID 57742597, compoundYield 87.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 20 mL scintillation vial, tert-butyl 3-((2-(5-bromo-3-phenoxypyridin-2-ylamino)thiazol-4-yl)methyl)-2-oxopyrrolidine-1-carboxylate (35 mg, 0.064 mmol) was dissolved in CH2Cl2 (1 mL) and HCl (4.0M solution in dioxane) (2.00 mL, 8.00 mmol) was added. The resulting mixture was agitated overnight. The solvents and excess HCl were evaporated, and product was obtained as yellow solid (25 mg, 87.5% yield). 1H NMR (DMSO-d6 δ 1.70-1.80 (m, 1H), 2.12-2.20 (m, 1H), 2.60-2.74 (m, 1H), 3.02 (d, 1H), 3.16-3.22 (m, 2H), 3.44-3.76 (m, 5H), 6.97 (s, 1H), 7.19-7.50 (m, 6H), 7.83 (s, 1H), 8.30 (s, 1H).

Workup

  1. customThe solvents and excess HCl were evaporated

Sources & evidence

ORD record
ord-56cd7559dd0f43abb57266f091572b99
Source dataset
uspto-grants-2011_09
Patent number
US08022223B2

Reaction notes

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