Hydrochloric Acid → HCID 136245905, compound

HRID 59560Notes

Reaction equation

HRID 59560 reaction equation
[CH:1]1([C:4]2[N:9]=[CH:8][C:7]([CH2:10][NH:11][C:12](=O)[O:13]C(C)(C)C)=[CH:6][C:5]=2[C:19]2[NH:23][C:22](=[O:24])[N:21]([C:25]3[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=3)[N:20]=2)[CH2:3][CH2:2]1.Cl>>[CH:1]1([C:4]2[N:9]=[CH:8][C:7]([CH2:10][NH:11][C:12](=[O:13])[C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][C:5]=2[C:19]2[NH:23][C:22](=[O:24])[N:21]([C:25]3[CH:30]=[CH:29][C:28]([C:31]([F:32])([F:34])[F:33])=[CH:27][CH:26]=3)[N:20]=2)[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 136612537tert-butyl (6-cyclopropyl-5-(1-(4-(trifluoromethyl)phenyl)-4,5-dihydro-5-oxo-1H-1,2,4-triazol-3-yl)pyridin-3-yl)methylcarbamate

Product 1

HCID 136245905HCID 136245905, compoundYield 41.4%

Procedure

Stirred a solution of tert-butyl (6-cyclopropyl-5-(1-(4-(trifluoromethyl)phenyl)-4,5-dihydro-5-oxo-1H-1,2,4-triazol-3-yl)pyridin-3-yl)methylcarbamate (0.100 g) in EtOC:HCl (5.0 mL) for 6 h at RT. Excess of solvent was removed and added DCM (5.0 mL), TEA (0.5 mL) and pivaloyl chloride (0.045 g) under nitrogen atmosphere o the reaction mixture. The reaction mass was stirred at RT for 4 h. Excess of solvent was removed under vacuum and the residue was diluted with water, extracted with EtOAC and concentrated to afford 0.020 g of the product. 1H NMR (300 MHz, DMSO d6): 0.98 (m, 4H), 1.12 (s, 9H), 2.73 (m, 1H), 4.27 (d, J=6.0 Hz, 2H), 7.78 (s, 1H), 7.85 (d, J=8.7 Hz, 2H), 8.13 (t, 1H), 8.19 (d, J=9.3 Hz, 2H), 8.40 (s, 1H), 12.75 (s, 1H); MS (m/z): 460.30 (M+H)+

Workup

  1. customExcess of solvent was removed
  2. additionadded DCM (5.0 mL), TEA (0.5 mL) and pivaloyl chloride (0.045 g) under nitrogen atmosphere o the reaction mixture
  3. customExcess of solvent was removed under vacuum
  4. additionthe residue was diluted with water
  5. extractionextracted with EtOAC
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-dea1227bf0124aba89a3d892b589eb17
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Reaction notes

Loading…