Benzoyl chloride → HCID 86703770, compound

HRID 1849891Notes

Reaction equation

HRID 1849891 reaction equation
[NH:1]1[CH2:4][CH:3]([CH2:5][O:6][C:7]2[C:16]([CH:17]3[CH2:19][CH2:18]3)=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:9]([F:20])[CH:8]=2)[CH2:2]1.[C:21](Cl)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N(CC)CC)C>C(Cl)Cl>[C:21]([N:1]1[CH2:4][CH:3]([CH2:5][O:6][C:7]2[C:16]([CH:17]3[CH2:19][CH2:18]3)=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:9]([F:20])[CH:8]=2)[CH2:2]1)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 86703762Methyl 4-(azetidin-3-ylmethoxy)-5-cyclopropyl-2-fluorobenzoate

Product 1

HCID 86703770HCID 86703770, compoundYield 101.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

To a mixture of methyl 4-(azetidin-3-ylmethoxy)-5-cyclopropyl-2-fluorobenzoate (50 mg, 0.18 mmol), benzoyl chloride (28 mg, 0.20 mmol), and triethylamine (36 mg, 0.36 mmol) in DCM (10 mL) was stirred at 20° C. for 1 hour. The mixture was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated to get a crude product (70 mg, 99%) which was used in the next step without further purification. LCMS (ESI) m/z: 384.1 [M+H]+.

Workup

  1. washThe mixture was washed with brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-04aa51747642407885c477427d83cf3c
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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