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

HRID 2092216Notes

Reaction equation

HRID 2092216 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([NH:10][C:11](=[N:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[C:17]([F:22])[CH:16]=2)SC)=O)[CH:5]=[C:4]([CH3:23])[N:3]=1.[NH:24]([CH2:26][C@@H:27]([OH:30])[CH2:28][CH3:29])[NH2:25]>CC(O)(C)C>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[N:24]([CH2:26][C@@H:27]([OH:30])[CH2:28][CH3:29])[N:25]=[C:11]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([F:21])=[C:17]([F:22])[CH:16]=3)[N:10]=2)[CH:5]=[C:4]([CH3:23])[N:3]=1

Participants

4

Reactant 2

HCID 28082624(S)-1-Hydrazino-butan-2-olHCID 1361160181-(2-Chloro-6-methyl-pyridine-4-carbonyl)-3-(3,4-difluoro-phenyl)-2-methyl-isothiourea

Product 1

HCID 86644737(S)-1-[5-(2-Chloro-6-methyl-pyridin-4-yl)-3-(3,4-difluoro-phenylamino)-[1,2,4]triazol-1-yl]-butan-2-ol

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

Intermediate D2 (1 g; 2.81 mmol) was dissolved in t-BuOH (40 ml) and, then intermediate D3 (0.44 g; 4.22 mmol) was added. The reaction mixture was stirred and refluxed for 4 hours and then the solvent was evaporated. The residue was purified by silica column chromatography (gradient: CH2Cl2/10% CH3OH in CH2Cl2 from 100/0 to 0/100). Yield: 1.1 g of intermediate D4 (S-enantiomer).

Workup

  1. temperaturerefluxed for 4 hours
  2. customthe solvent was evaporated
  3. customThe residue was purified by silica column chromatography (gradient: CH2Cl2/10% CH3OH in CH2Cl2 from 100/0 to 0/100)

Sources & evidence

ORD record
ord-5cad52bd32f44315ac6e48f044a984ec
Source dataset
uspto-grants-2013_05
Patent number
US08440701B2

Reaction notes

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