(S)-1-Hydrazino-butan-2-ol → (S)-1-[5-(2-Chloro-6-methyl-pyridin-4-yl)-3-(3-methoxy-5-trifluoromethyl-phenylamino)-[1,2,4]triazol-1-yl]butan-2-ol

HRID 2092219Notes

Reaction equation

HRID 2092219 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([NH:10][C:11](=[N:14][C:15]2[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[C:17]([O:25][CH3:26])[CH:16]=2)SC)=O)[CH:5]=[C:4]([CH3:27])[N:3]=1.[NH:28]([CH2:30][C@@H:31]([OH:34])[CH2:32][CH3:33])[NH2:29]>C(O)C>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[N:28]([CH2:30][C@@H:31]([OH:34])[CH2:32][CH3:33])[N:29]=[C:11]([NH:14][C:15]3[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[C:17]([O:25][CH3:26])[CH:16]=3)[N:10]=2)[CH:5]=[C:4]([CH3:27])[N:3]=1

Participants

4

Reactant 2

HCID 28082624(S)-1-Hydrazino-butan-2-olHCID 1361160191-(2-Chloro-6-methyl-pyridine-4-carbonyl)-3-(3-methoxy-5-trifluoromethyl-phenyl)-2-methyl-isothiourea

Product 1

HCID 86644738(S)-1-[5-(2-Chloro-6-methyl-pyridin-4-yl)-3-(3-methoxy-5-trifluoromethyl-phenylamino)-[1,2,4]triazol-1-yl]butan-2-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of intermediate D6 (8.356 g, 0.020 mol) and intermediate D3 (2.083 g, 0.020 mol) in ethanol (200 ml) was stirred overnight at reflux. Subsequently, the solvent was evaporated to yield intermediate D7 (S-enantiomer) as a yellow oil that was used as such in the next reaction step.

Workup

  1. temperatureat reflux
  2. customSubsequently, the solvent was evaporated

Sources & evidence

ORD record
ord-cc7f36bb7fdf4c8aa52c4d36de27cd7f
Source dataset
uspto-grants-2013_05
Patent number
US08440701B2

Reaction notes

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