Benzyl 4-(4-(2-imino-2-methoxyethyl)pyridin-2-yl)piperazine-1-carboxylate → benzyl 4-(4-((2-methyl-5-(3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazol-5-yl)-2H-1,2,4-triazol-3-yl)methyl)pyridin-2-yl)piperazine-1-carboxylate

HRID 517564Notes

Reaction equation

HRID 517564 reaction equation
[NH:1]=[C:2](OC)[CH2:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]([N:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:17])[CH2:12][CH2:11]2)[CH:5]=1.[CH3:28][NH:29][NH:30][C:31]([C:33]1[O:37][N:36]=[C:35]([C:38]2[CH:43]=[CH:42][C:41]([O:44][C:45]([F:48])([F:47])[F:46])=[CH:40][CH:39]=2)[N:34]=1)=O>CO>[CH3:28][N:29]1[C:2]([CH2:3][C:4]2[CH:9]=[CH:8][N:7]=[C:6]([N:10]3[CH2:11][CH2:12][N:13]([C:16]([O:18][CH2:19][C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)=[O:17])[CH2:14][CH2:15]3)[CH:5]=2)=[N:1][C:31]([C:33]2[O:37][N:36]=[C:35]([C:38]3[CH:39]=[CH:40][C:41]([O:44][C:45]([F:48])([F:46])[F:47])=[CH:42][CH:43]=3)[N:34]=2)=[N:30]1

Participants

4

Reactant 2

HCID 86711502Benzyl 4-(4-(2-imino-2-methoxyethyl)pyridin-2-yl)piperazine-1-carboxylateHCID 86711504HCID 86711504, compound

Product 1

HCID 86711503benzyl 4-(4-((2-methyl-5-(3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazol-5-yl)-2H-1,2,4-triazol-3-yl)methyl)pyridin-2-yl)piperazine-1-carboxylateYield 30.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of benzyl 4-(4-(2-imino-2-methoxyethyl)pyridin-2-yl)piperazine-1-carboxylate (500 mg, 1.5 mmol) and TEA (1 mL, 7.5 mmol) in dry MeOH (5 mL), N′-methyl-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole-5-carbohydrazide (450 mg, 1.5 mmol) was added slowly at 0° C. The mixture was stirred at 80° C. for 3 h, and then concentrated to give the crude product, which was purified by reverse phase chromatography (Mobile phase: MeCN/H2O containing 0.01% TFA, 50%˜60%) to afford benzyl 4-(4-((2-methyl-5-(3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazol-5-yl)-2H-1,2,4-triazol-3-yl)methyl)pyridin-2-yl)piperazine-1-carboxylate as a white solid (280 mg, 27%). MS (ES+) C30H27F3N8O4 requires: 620, found: 621 [M+H]+.

Workup

  1. concentrationconcentrated
  2. customto give the crude product, which
  3. customwas purified by reverse phase chromatography (Mobile phase: MeCN/H2O containing 0.01% TFA, 50%˜60%)

Sources & evidence

ORD record
ord-caeac8d647464af89b2db603ad99b020
Source dataset
uspto-grants-2015_08
Patent number
US09115120B2

Reaction notes

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