Sodium Bicarbonate → N-ethyl-2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)ethanamine

HRID 1772465Notes

Reaction equation

HRID 1772465 reaction equation
[CH2:1]([N:3]([CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[N:23]=[CH:22][N:21]([C:24]3[CH:29]=[CH:28][C:27]([O:30][C:31]([F:34])([F:33])[F:32])=[CH:26][CH:25]=3)[N:20]=2)=[CH:15][CH:14]=1)C(=O)OC(C)(C)C)[CH3:2].C(=O)(O)[O-].[Na+]>>[CH2:1]([NH:3][CH2:11][CH2:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2[N:23]=[CH:22][N:21]([C:24]3[CH:29]=[CH:28][C:27]([O:30][C:31]([F:32])([F:34])[F:33])=[CH:26][CH:25]=3)[N:20]=2)=[CH:17][CH:18]=1)[CH3:2]

Participants

3

Reactant 2

HCID 516892Sodium BicarbonateHCID 90413631tert-butyl ethyl(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenethyl)carbamate

Product 1

HCID 90412668N-ethyl-2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)ethanamine

Procedure

The title compound was prepared from tert-butyl ethyl(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenethyl)carbamate (CB64), neutralized with aqueous sodium bicarbonate, and isolated as an orange solid (0.167 g, 98%, 80% pure): 1H NMR (400 MHz, CDCl3) δ 8.54 (s, 1H), 8.17-8.06 (m, 2H), 7.87-7.63 (m, 2H), 7.37 (dt, J=8.0, 1.0 Hz, 2H), 7.34-7.28 (m, 2H), 3.21 (s, 2H), 3.14-2.97 (m, 4H), 1.84 (s, 1H), 0.87 (ddd, J=12.0, 8.9, 6.6 Hz, 3H); 19F NMR (376 MHz, CDCl3) δ −58.04; ESIMS m/z 377 ([M+H]+).

Workup

  1. customisolated as an orange solid (0.167 g, 98%, 80% pure)

Sources & evidence

ORD record
ord-0b23cbd546654d609511c7d3175bd489
Source dataset
uspto-grants-2016_02
Patent number
US09249133B2

Reaction notes

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