Sodium Bicarbonate → Trifluoroacetic acid

HRID 924216Notes

Reaction equation

HRID 924216 reaction equation
[CH3:1][N:2]([CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[N:22]=[CH:21][N:20]([C:23]3[CH:28]=[CH:27][C:26]([O:29][C:30]([F:33])([F:32])[F:31])=[CH:25][CH:24]=3)[N:19]=2)=[CH:14][CH:13]=1)C(=O)OC(C)(C)C.[C:34](=O)([OH:36])[O-:35].[Na+]>>[CH3:1][NH:2][CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]2[N:22]=[CH:21][N:20]([C:23]3[CH:28]=[CH:27][C:26]([O:29][C:30]([F:33])([F:31])[F:32])=[CH:25][CH:24]=3)[N:19]=2)=[CH:16][CH:17]=1.[F:33][C:30]([F:31])([F:32])[C:34]([OH:36])=[O:35]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 90412594tert-butyl methyl(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenethyl)carbamate

Product 2

HCID 6422Trifluoroacetic acidYield 111%HCID 90411907N-methyl-2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)ethanamine

Procedure

The title compound was prepared from tert-butyl methyl(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenethyl)carbamate (CB63), neutralized with aqueous sodium bicarbonate, and isolated as a yellow waxy solid with excess trifluoroacetic acid (5.73 g, 111%): 1H NMR (400 MHz, CDCl3) δ 8.53 (s, 1H), 8.12 (d, J=8.2 Hz, 2H), 7.77 (d, J=9.0 Hz, 2H), 7.37 (dd, J=9.0, 1.0 Hz, 2H), 7.31 (d, J=8.2 Hz, 2H), 3.23-3.12 (m, 2H), 3.05 (dd, J=9.4, 6.3 Hz, 2H), 2.67 (s, 3H), 1.29-1.22 (m, 1H); 19F NMR (376 MHz, CDCl3) δ −58.04, −75.71; ESIMS m/z 363 ([M+H]+).

Sources & evidence

ORD record
ord-10d632b3f4d24e3bbfdd38467c904930
Source dataset
uspto-grants-2016_03
Patent number
US09278964B2

Reaction notes

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