HCID 57443624, compound → HCID 67145169, compound

HRID 909265Notes

Reaction equation

HRID 909265 reaction equation
[Br:1][C:2]1[C:3]([S:11][C:12]2[N:13](CC3C=CC(OC)=CC=3)[C:14]3[CH:19]=[CH:18][N:17]=[C:16]([NH2:20])[C:15]=3[N:21]=2)=[CH:4][C:5]2[O:9][CH2:8][O:7][C:6]=2[CH:10]=1>C(O)(C(F)(F)F)=O>[Br:1][C:2]1[C:3]([S:11][C:12]2[NH:13][C:14]3[CH:19]=[CH:18][N:17]=[C:16]([NH2:20])[C:15]=3[N:21]=2)=[CH:4][C:5]2[O:9][CH2:8][O:7][C:6]=2[CH:10]=1

Participants

3

Reactant 1

HCID 57443624HCID 57443624, compound

Product 1

HCID 67145169HCID 67145169, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
80 °C

Procedure

2-[(6-Bromo-1,3-benzodioxol-5-yl)sulfanyl]-1-(4-methoxybenzyl)-1H-imidazo[4,5-c]pyridin-4-amine (999 mg, 2.05 mmol) was dissolved in TFA (8 mL) and the mixture was heated at 80° C. for 7 h. Upon completion of the reaction, the mixture was concentrated in vacuum and the residual TFA was azeotropically removed with toluene. The resulting residue was diluted with water and was adjusted to pH 7 by satd. NaHCO3. The product portion was extracted with EtOAc, washed with brine, dried (Na2SO4), filtered, and concentrated in vacuum. The residue was then triturated with EtOAc, filtered, washed with EA, and dried to afford the title compound (588 mg, 79%). Additional product (126 mg, 17%) was obtained by column (SiO2, MeOH/CH2Cl2, 0 to 10%) purification of the combined filtrates: 1H NMR (DMSO-d6) δ 7.53 (d, J=6.4 Hz, 1H), 7.39 (s, 1H), 7.16-7.08 (brs, 2H), 7.07 (s, 1H), 6.79 (d, J=6.4 Hz, 1H), 6.12 (s, 2H); LC-MS [M+H]+ 366.97.

Workup

  1. customUpon completion of the reaction
  2. concentrationthe mixture was concentrated in vacuum
  3. customthe residual TFA was azeotropically removed with toluene
  4. additionThe resulting residue was diluted with water
  5. extractionThe product portion was extracted with EtOAc
  6. washwashed with brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuum
  10. customThe residue was then triturated with EtOAc
  11. filtrationfiltered
  12. washwashed with EA
  13. customdried

Sources & evidence

ORD record
ord-f57ddbf0f4264314807878b07b565223
Source dataset
uspto-grants-2011_09
Patent number
US08017780B1

Reaction notes

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