Triethylamine → 3-{[4-(Azetidin-1-ylcarbonyl)phenyl]oxy}-N-(1-ethyl-1H-pyrazol-3-yl)-5-{[(1S)-2-hydroxy-1-methylethyl]oxy}benzamide

HRID 20528Notes

Reaction equation

HRID 20528 reaction equation
[N:1]1([C:5]([C:7]2[CH:12]=[CH:11][C:10]([O:13][C:14]3[CH:15]=[C:16]([CH:27]=[C:28]([O:30][C@@H:31]([CH3:34])[CH2:32][OH:33])[CH:29]=3)[C:17]([NH:19][C:20]3[CH:24]=[CH:23][N:22]([CH2:25][CH3:26])[N:21]=3)=[O:18])=[C:9](Cl)[CH:8]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C>C1COCC1.CO>[N:1]1([C:5]([C:7]2[CH:8]=[CH:9][C:10]([O:13][C:14]3[CH:15]=[C:16]([CH:27]=[C:28]([O:30][C@@H:31]([CH3:34])[CH2:32][OH:33])[CH:29]=3)[C:17]([NH:19][C:20]3[CH:24]=[CH:23][N:22]([CH2:25][CH3:26])[N:21]=3)=[O:18])=[CH:11][CH:12]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 117130403-{[4-(azetidin-1-ylcarbonyl)-2-chlorophenyl]oxy}-N-(1-ethyl-1H-pyrazol-3-yl)-5-{[(1S)-2-hydroxy-1-methylethyl]oxy}benzamide

Product 1

HCID 116268333-{[4-(Azetidin-1-ylcarbonyl)phenyl]oxy}-N-(1-ethyl-1H-pyrazol-3-yl)-5-{[(1S)-2-hydroxy-1-methylethyl]oxy}benzamideYield 73%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-{[4-(azetidin-1-ylcarbonyl)-2-chlorophenyl]oxy}-N-(1-ethyl-1H-pyrazol-3-yl)-5-{[(1S)-2-hydroxy-1-methylethyl]oxy}benzamide (246 mg, 0.504 mmol) and triethylamine (0.42 mL, 3.02 mmol) in THF (6 mL) and methanol (6 mL) was evacuated and purged with argon (×3). Palladium on carbon (10% w/w, 52 mg) was added and reaction mixture was evacuated and finally filled with hydrogen gas. The reaction mixture was left to stir at ambient temperature under hydrogen for 2 hours. The Pd/C was filtered off and mixture partitioned between ethyl acetate and 1M hydrochloric acid solution. The organic phase was dried (MgSO4) and the filtrate concentrated in vacuo to give the product (170 mg, 73%).

Workup

  1. custompurged with argon (×3)
  2. additionPalladium on carbon (10% w/w, 52 mg) was added
  3. customreaction mixture
  4. customwas evacuated
  5. additionfinally filled with hydrogen gas
  6. waitThe reaction mixture was left
  7. filtrationThe Pd/C was filtered off
  8. custommixture partitioned between ethyl acetate and 1M hydrochloric acid solution
  9. dry with materialThe organic phase was dried (MgSO4)
  10. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-3ea83e182c104d1a8c4d70ce0973c303
Source dataset
uspto-grants-2010_06
Patent number
US07745475B2

Reaction notes

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