Trifluoroacetic acid → 5-Bromo-3-(5-(2,3-dichlorophenyl)thiazol-4-yl)pyridin-2-amine

HRID 253978Notes

Reaction equation

HRID 253978 reaction equation
COC1C=CC(C[NH:8][C:9]2[C:14]([C:15]3[N:16]=[CH:17][S:18][C:19]=3[C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:21]=3[Cl:27])=[CH:13][C:12]([Br:28])=[CH:11][N:10]=2)=CC=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Br:28][C:12]1[CH:13]=[C:14]([C:15]2[N:16]=[CH:17][S:18][C:19]=2[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:21]=2[Cl:27])[C:9]([NH2:8])=[N:10][CH:11]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58179565N-(4-methoxybenzyl)-5-bromo-3-(5-(2,3-dichlorophenyl)thiazol-4-yl)pyridin-2-amine

Product 1

HCID 581795705-Bromo-3-(5-(2,3-dichlorophenyl)thiazol-4-yl)pyridin-2-amineYield 2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-(4-methoxybenzyl)-5-bromo-3-(5-(2,3-dichlorophenyl)thiazol-4-yl)pyridin-2-amine (110 mg) and TFA (100 μL) in methylene chloride (2 mL) was stirred at 40° C. overnight. The reaction was concentrated and purified by reversed-phase HPLC to give 5-bromo-3-(5-(2,3-dichlorophenyl)thiazol-4-yl)pyridin-2-amine as a white solid [1.1 mg, 2% yield; LC-MS M+H=519.9; 1H-NMR (300 MHz, methanol-d4) 9.17 (1H, d), 7.95 (1H, d), 7.60-7.63 (2H, m), 7.34-7.35 (1H, m), 7.27 (1H, dd)].

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified by reversed-phase HPLC

Sources & evidence

ORD record
ord-fb2d331cd46c4177ad9497fee03ffd3f
Source dataset
uspto-grants-2011_01
Patent number
US07872031B2

Reaction notes

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