Hydrochloric Acid → 1-[(3,4-Dichlorophenyl)methyl]-N-{4-[(2-hydroxyethyl)oxy]phenyl}-5-methyl-1H-1,2,3-triazole-4-carboxamide

HRID 2170544Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][N:10]2[C:14]([CH3:15])=[C:13]([C:16]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][O:28]C4CCCCO4)=[CH:21][CH:20]=3)=[O:17])[N:12]=[N:11]2)[CH:5]=[CH:6][C:7]=1[Cl:8].Cl>CO.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][N:10]2[C:14]([CH3:15])=[C:13]([C:16]([NH:18][C:19]3[CH:20]=[CH:21][C:22]([O:25][CH2:26][CH2:27][OH:28])=[CH:23][CH:24]=3)=[O:17])[N:12]=[N:11]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of the crude 1-[(3,4-dichlorophenyl)methyl]-5-methyl-N-(4-{[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]oxy}phenyl)-1H-1,2,3-triazole-4-carboxamide (Intermediate 19) in methanol was added a saturated solution of HCl in ethyl acetate. The reaction was stirred to 60° C. for 18 hours. After evaporation, the title compound was obtained as a cream solid after recrystallisation from methanol (0.23 g, 54% from intermediate 6). HRMS calculated for C19H18Cl2N4O3 (M+H)+ 421.0834. found: 421.0837, Rt: 2.76 min. MP: 140° C.

Workup

customAfter evaporation

Sources & evidence

ORD record: ord-51e2faea66c147a0966868cc6a0a8955
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09051281B2

Reaction notes

Loading…