3-Methoxypropylamine → N-(3-methoxylpropyl)-3-((5-methyl-3-(3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazol-5-yl)-1H-1,2,4-triazol-1-yl)methyl)benzamide

HRID 1475214Notes

Reaction equation

HRID 1475214 reaction equation
[CH3:1][C:2]1[N:6]([CH2:7][C:8]2[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=2)[C:11](OC)=[O:12])[N:5]=[C:4]([C:18]2[O:22][N:21]=[C: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)[N:3]=1.[O:34]([CH2:36][CH2:37][CH2:38][NH2:39])[CH3:35].N1C=NC=N1.C1CCN2C(=NCCC2)CC1>>[O:34]([CH2:36][CH2:37][CH2:38][NH:39][C:11](=[O:12])[C:10]1[CH:15]=[CH:16][CH:17]=[C:8]([CH2:7][N:6]2[C:2]([CH3:1])=[N:3][C:4]([C:18]3[O:22][N:21]=[C:20]([C:23]4[CH:28]=[CH:27][C:26]([O:29][C:30]([F:31])([F:33])[F:32])=[CH:25][CH:24]=4)[N:19]=3)=[N:5]2)[CH:9]=1)[CH3:35]

Participants

5

Reactant 4

HCID 16723-MethoxypropylamineHCID 92571H-1,2,4-TriazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86711907methyl 3-((5-methyl-3-(3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazol-5-yl)-1H-1,2,4-triazol-1-yl)methyl)benzoate

Product 1

HCID 86711909N-(3-methoxylpropyl)-3-((5-methyl-3-(3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazol-5-yl)-1H-1,2,4-triazol-1-yl)methyl)benzamideYield 87.1%

Conditions

Temperature
70 °C

Procedure

A mixture of methyl 3-((5-methyl-3-(3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazol-5-yl)-1H-1,2,4-triazol-1-yl)methyl)benzoate (46 mg, 0.1 mmol) and 3-methoxylpropylamine (27 mg, 0.3 mmol) was treated with 1,2,4-triazole (7 mg, 0.1 mmol) and DBU (15 mg, 0.1 mmol), and heated to 70° C. overnight. The crude product was purified by a silica gel column with EtOAc to give N-(3-methoxylpropyl)-3-((5-methyl-3-(3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazol-5-yl)-1H-1,2,4-triazol-1-yl)methyl)benzamide as a white solid (45 mg, 87%). MS (ES+) C24H23F3N6O4 requires: 516. found: 517 [M+H]+. 1H NMR (600 MHz, CDCl3) δ 8.28 (d, J=8.8 Hz, 2H), 7.77 (s, 1H), 7.68 (d, J=7.7 Hz, 1H), 7.45 (t, J=7.7 Hz, 1H), 7.37 (d, J=7.9 Hz, 1H), 7.35 (d, J=8.3 Hz, 2H), 5.50 (s, 2H), 3.60-3.55 (m, 4H), 3.38 (s, 3H), 2.55 (s, 3H), 1.91-1.86 (m, 2H).

Workup

  1. customThe crude product was purified by a silica gel column with EtOAc

Sources & evidence

ORD record
ord-197070e841be451d8b18dd8a1ebd0ffd
Source dataset
uspto-grants-2015_04
Patent number
US09018380B2

Reaction notes

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