Trifluoroacetic acid → HCID 58179777, compound

HRID 253964Notes

Reaction equation

HRID 253964 reaction equation
COC1C=CC(C[NH:8][C:9]2[C:14]([C:15]3[N:16]=[N: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]=[N: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 58179970HCID 58179970, compound

Product 1

HCID 58179777HCID 58179777, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of N-(4-methoxybenzyl)-5-bromo-3-(5-(2,3-dichlorophenyl)-1,2,3-thiadiazol-4-yl)pyridin-2-amine (0.128 mmol) in CH2Cl2 (2 mL) was added TFA (3 mL). The mixture was heated at 40° C. for 20 hours then at RT for 3 d. The volatiles were evaporated and the residue purified by preparative reversed-phase HPLC to afford 5-bromo-3-(5-(2,3-dichlorophenyl)-1,2,3-thiadiazol-4-yl)pyridin-2-amine as a colorless oil (0.019 g, 37% yield). Using the same procedure, 5-bromo-3-(5-(2,3-fluorophenyl)-1,2,3-thiadiazol-4-yl)pyridin-2-amine and 5-bromo-3-(5-(3-chloro-2-fluorophenyl)-1,2,3-thiadiazol-4-yl)pyridin-2-amine can be produced from 1-(5-bromo-2-chloropyridin-3-yl)-2-(2,3-difluorophenyl)ethanone and 1-(5-bromo-2-chloropyridin-3-yl)-2-(3-chloro-2-fluorophenyl)ethanone, respectively.

Workup

  1. customThe volatiles were evaporated
  2. customthe residue purified by preparative reversed-phase HPLC

Sources & evidence

ORD record
ord-9d65212fe06e4b7a9357ba9e5b472e3f
Source dataset
uspto-grants-2011_01
Patent number
US07872031B2

Reaction notes

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