3-[4-(Azetidin-1-ylcarbonyl)-2-chlorophenoxy]-5-[(1S)-2-hydroxy-1-methylethoxy]-N-(1-isopropyl-1H-pyrazol-3-yl)benzamide → 3-[4-(Azetidin-1-ylcarbonyl)phenoxy]-5-[(1S)-2-hydroxy-1-methylethoxy]-N-(1-isopropyl-1H-pyrazol-3-yl)benzamide

HRID 20541Notes

Reaction equation

HRID 20541 reaction equation
[N:1]1([C:5]([C:7]2[CH:35]=[CH:34][C:10]([O:11][C:12]3[CH:13]=[C:14]([CH:26]=[C:27]([O:29][C@@H:30]([CH3:33])[CH2:31][OH:32])[CH:28]=3)[C:15]([NH:17][C:18]3[CH:22]=[CH:21][N:20]([CH:23]([CH3:25])[CH3:24])[N:19]=3)=[O:16])=[C:9](Cl)[CH:8]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1>CO>[N:1]1([C:5]([C:7]2[CH:35]=[CH:34][C:10]([O:11][C:12]3[CH:13]=[C:14]([CH:26]=[C:27]([O:29][C@@H:30]([CH3:33])[CH2:31][OH:32])[CH:28]=3)[C:15]([NH:17][C:18]3[CH:22]=[CH:21][N:20]([CH:23]([CH3:25])[CH3:24])[N:19]=3)=[O:16])=[CH:9][CH:8]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 115553263-[4-(Azetidin-1-ylcarbonyl)-2-chlorophenoxy]-5-[(1S)-2-hydroxy-1-methylethoxy]-N-(1-isopropyl-1H-pyrazol-3-yl)benzamide

Product 1

HCID 116343363-[4-(Azetidin-1-ylcarbonyl)phenoxy]-5-[(1S)-2-hydroxy-1-methylethoxy]-N-(1-isopropyl-1H-pyrazol-3-yl)benzamideYield 48.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-[4-(Azetidin-1-ylcarbonyl)-2-chlorophenoxy]-5-[(1S)-2-hydroxy-1-methylethoxy]-N-(1-isopropyl-1H-pyrazol-3-yl)benzamide (0.33 g, 0.644 mmol) was dissolved in methanol (4 mL) and THF (4 mL) and the flask evacuated and purged with argon (3 times). 10% Palladium on carbon (0.033 g) was added and the flask further evacuated and finally purged with hydrogen gas. The reaction mixture was stirred at ambient temperature for 20 hours. The reaction mixture was evacuated and purged with nitrogen (3 times). The catalyst was filtered off through celite, and the filtrate concentrated in vacuo. The residue was chromatographed on silica eluting with a gradient of 0-100% ethyl acetate in isohexane to give the desired compound (0.15 g);

Workup

  1. customTHF (4 mL) and the flask evacuated
  2. custompurged with argon (3 times)
  3. addition10% Palladium on carbon (0.033 g) was added
  4. customthe flask further evacuated
  5. customfinally purged with hydrogen gas
  6. customThe reaction mixture was evacuated
  7. custompurged with nitrogen (3 times)
  8. filtrationThe catalyst was filtered off through celite
  9. concentrationthe filtrate concentrated in vacuo
  10. customThe residue was chromatographed on silica eluting with a gradient of 0-100% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-80bc57c20d4b46a0963c262431485386
Source dataset
uspto-grants-2010_06
Patent number
US07745475B2

Reaction notes

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