Potassium Carbonate → 4-[5-({1-[2-(3-chlorophenyl)-2H-tetrazol-5-yl]ethyl}thio)-4-cyclopropyl-4H-1,2,4-triazol-3-yl]pyridine

HRID 639799Notes

Reaction equation

HRID 639799 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[N:12]=[N:11][C:10]([CH:13](OS(C)(=O)=O)[CH3:14])=[N:9]2)[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH:26]1([N:29]2[C:33]([C:34]3[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=3)=[N:32][NH:31][C:30]2=[S:40])[CH2:28][CH2:27]1>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[N:12]=[N:11][C:10]([CH:13]([S:40][C:30]3[N:29]([CH:26]4[CH2:28][CH2:27]4)[C:33]([C:34]4[CH:35]=[CH:36][N:37]=[CH:38][CH:39]=4)=[N:32][N:31]=3)[CH3:14])=[N:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 49625494-cyclopropyl-5-(pyridin-4-yl)-4H-1,2,4-triazole-3-thiolHCID 75292157methanesulfonic acid 1-[2-(3-chlorophenyl)-2H-tetrazol-5-yl]-ethyl ester

Product 1

HCID 116332374-[5-({1-[2-(3-chlorophenyl)-2H-tetrazol-5-yl]ethyl}thio)-4-cyclopropyl-4H-1,2,4-triazol-3-yl]pyridineYield 68.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound (25.2 mg, 68%, white solid) was prepared from methanesulfonic acid 1-[2-(3-chlorophenyl)-2H-tetrazol-5-yl]-ethyl ester (26.4 mg, 0.087 mmol) using potassium carbonate (13.3 mg, 0.096 mmol) and 4-cyclopropyl-5-pyridin-4-yl-2,4-dihydro-[1,2,4]triazole-3-thione (19.0 mg, 0.087 mmol) in acetonitrile (3 mL) at room temperature overnight. The reaction mixture was purified by chromatography using a silica SPE tube (2% methanol in dichloromethane). 1H NMR (CDCl3) δ (ppm): 8.78 (d, 2H), 8.16 (s, 1H), 8.04 (m, 1H), 7.75 (d, 2H), 7.49 (m, 2H), 5.67 (q, 1H), 3.24 (m, 1H), 2.08 (d, 3H), 1.16 (m, 2H), 0.82 (m, 2H).

Workup

  1. customat room temperature
  2. customovernight
  3. customThe reaction mixture was purified by chromatography

Sources & evidence

ORD record
ord-0b77a743c70747ac8c8981b3ab1b9f99
Source dataset
uspto-grants-2010_04
Patent number
US07691892B2

Reaction notes

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