Triethylamine → Wvg4bzb398

HRID 20514Notes

Reaction equation

HRID 20514 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:26]=[C:27]([O:29][C@@H:30]([CH3:33])[CH2:31][OH:32])[CH:28]=3)[C:17]([NH:19][C:20]3[CH:24]=[CH:23][N:22]([CH3:25])[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>CO.C1COCC1>[N:1]1([C:5]([C:7]2[CH:8]=[CH:9][C:10]([O:13][C:14]3[CH:15]=[C:16]([CH:26]=[C:27]([O:29][C@@H:30]([CH3:33])[CH2:31][OH:32])[CH:28]=3)[C:17]([NH:19][C:20]3[CH:24]=[CH:23][N:22]([CH3:25])[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 115839093-{[4-(Azetidin-1-ylcarbonyl)-2-chlorophenyl]oxy}-5-{[(1S)-2-hydroxy-1-methylethyl]oxy}N-(1-methyl-1H-pyrazol-3-yl)benzamide

Product 1

HCID 11604824Wvg4bzb398Yield 98.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-{[4-(Azetidin-1-ylcarbonyl)-2-chlorophenyl]oxy}-5-{[(1S)-2-hydroxy-1-methylethyl]oxy}-N-(1-methyl-1H-pyrazol-3-yl)benzamide (104 mg, 0.215 mmol) was dissolved in methanol (3 mL) and THF (3 mL). Triethylamine (65 mg, 0.644 mmol) was added and the flask evacuated and purged with nitrogen (3 times). 10% Palladium on carbon (25 mg) was added and the flask further evacuated and finally purged with hydrogen gas. The reaction mixture was stirred at ambient temperature for 16 hours until completion. The reaction mixture was evacuated and purged with nitrogen (3 times). The catalyst was filtered off, the filtrate concentrated in vacuo and dissolved in ethyl acetate (10 mL), washed with water (2×10 mL, saturated aqueous sodium chloride solution (10 mL) and dried (MgSO4) to give the title compound (95 mg).

Workup

  1. customthe flask evacuated
  2. custompurged with nitrogen (3 times)
  3. addition10% Palladium on carbon (25 mg) 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
  9. concentrationthe filtrate concentrated in vacuo
  10. dissolutiondissolved in ethyl acetate (10 mL)
  11. washwashed with water (2×10 mL, saturated aqueous sodium chloride solution (10 mL)
  12. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-e36a0b6e73b24f56a314acfc20d3a95e
Source dataset
uspto-grants-2010_06
Patent number
US07745475B2

Reaction notes

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