(S)-1-Hydrazino-butan-2-ol → (S)-1-[5-(2,6-Dichloro-pyridin-4-yl)-3-(2,3,4-trifluoro-phenylamino)-[1,2,4]triazol-1-yl]-butan-2-ol

HRID 2092223Notes

Reaction equation

HRID 2092223 reaction equation
[NH:1]([CH2:3][C@@H:4]([OH:7])[CH2:5][CH3:6])[NH2:2].[Cl:8][C:9]1[CH:14]=[C:13]([C:15]([NH:17][C:18](=[N:21][C:22]2[CH:27]=[CH:26][C:25]([F:28])=[C:24]([F:29])[C:23]=2[F:30])SC)=O)[CH:12]=[C:11]([Cl:31])[N:10]=1>CC(O)(C)C>[Cl:8][C:9]1[CH:14]=[C:13]([C:15]2[N:1]([CH2:3][C@@H:4]([OH:7])[CH2:5][CH3:6])[N:2]=[C:18]([NH:21][C:22]3[CH:27]=[CH:26][C:25]([F:28])=[C:24]([F:29])[C:23]=3[F:30])[N:17]=2)[CH:12]=[C:11]([Cl:31])[N:10]=1

Participants

4

Reactant 2

HCID 28082624(S)-1-Hydrazino-butan-2-olHCID 1361160171-(2,6-Dichloro-pyridine-4-carbonyl)-2-methyl-3-(2,3,4-trifluoro-phenyl)isothiourea

Product 1

HCID 86644740(S)-1-[5-(2,6-Dichloro-pyridin-4-yl)-3-(2,3,4-trifluoro-phenylamino)-[1,2,4]triazol-1-yl]-butan-2-ol

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

Intermediate D3 (0.143 g, 0.00137 mol) was added to a solution of intermediate D10 (0.3 g, 0.000457 mol) in t-BuOH (40 ml). The reaction mixture was stirred overnight at reflux. The solvent was evaporated in vacuo and the residue was purified by flash column chromatography over silica gel (eluent: EtOAc/heptane gradient from 20/80 to 50/50). The desired fractions were collected and the solvent was evaporated. Yield: 0.160 g of intermediate D11 (81%; S-enantiomer).

Workup

  1. temperatureat reflux
  2. customThe solvent was evaporated in vacuo
  3. customthe residue was purified by flash column chromatography over silica gel (eluent: EtOAc/heptane gradient from 20/80 to 50/50)
  4. customThe desired fractions were collected
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-74f4d259222345e1ae152ba609f86bdb
Source dataset
uspto-grants-2013_05
Patent number
US08440701B2

Reaction notes

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