Thiophene → 1-[3-(3,4-Difluoro-phenylamino)-5-(2-methyl-pyridin-4-yl)-[1,2,4]triazol-1-yl]-hexan-2-ol

HRID 2092227Notes

Reaction equation

HRID 2092227 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[N:12]([CH2:13][C@@H:14]([OH:17])[CH2:15][CH3:16])[N:11]=[C:10]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([F:25])=[C:21]([F:26])[CH:20]=3)[N:9]=2)[CH:5]=[C:4]([CH3:27])[N:3]=1.[CH3:28][CH2:29]N(CC)CC.S1C=CC=C1>C1COCC1.[Pd]>[F:26][C:21]1[CH:20]=[C:19]([NH:18][C:10]2[N:9]=[C:8]([C:6]3[CH:7]=[CH:2][N:3]=[C:4]([CH3:27])[CH:5]=3)[N:12]([CH2:13][CH:14]([OH:17])[CH2:15][CH2:16][CH2:28][CH3:29])[N:11]=2)[CH:24]=[CH:23][C:22]=1[F:25]

Participants

6

Reactant 3

HCID 8030ThiopheneHCID 8471TriethylamineHCID 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

Product 1

HCID 594558881-[3-(3,4-Difluoro-phenylamino)-5-(2-methyl-pyridin-4-yl)-[1,2,4]triazol-1-yl]-hexan-2-ol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of intermediate, 1-[5-(2-chloro-6-methyl-pyridin-4-yl)-3-(3,4-difluoro-phenylamino)-[1,2,4]triazol-1-yl]-hexan-2-ol (prepared according to D4) (1.5 g; 3.5 mmol) and Et3N (2 ml) in THF (40 ml) was hydrogenated with Pd/C 10% (0.020 g) as a catalyst in the presence of thiophene solution (0.1 ml; 4% in DIPE). After uptake of H2 (1 equiv) had ceased, the catalyst was filtered off and the filtrate was evaporated in vacuo. The residue was suspended in DIPE and filtrated. The crystals were dried in a vacuum oven at 70° C. overnight.

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated in vacuo
  3. filtrationfiltrated
  4. customThe crystals were dried in a vacuum oven at 70° C. overnight

Sources & evidence

ORD record
ord-12adb2a7895f46cb9bb3ca04cbdcfd78
Source dataset
uspto-grants-2013_05
Patent number
US08440701B2

Reaction notes

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