Water → HCID 90021241, compound

HRID 2200196Notes

Reaction equation

HRID 2200196 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]([CH:8]=[CH:9][C:10]=2[F:11])[NH2:7])[CH2:3][CH2:2]1.Cl[C:13]([O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:14].N1C=CC=CC=1.O>C(Cl)Cl>[CH:1]1([C:4]2[CH:5]=[C:6]([NH:7][C:13](=[O:14])[O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:8]=[CH:9][C:10]=2[F:11])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 15891Phenyl chloroformateHCID 574163033-Cyclopropyl-4-fluoroaniline

Product 1

HCID 90021241HCID 90021241, compoundYield 32.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

Add 3-cyclopropyl-4-fluoro-aniline (600 mg, 3.97 mmol), phenyl chloroformate (620 mg, 3.97 mmol) and pyridine (314 mg, 3.97 mmol) in DCM (30 mL), stir at room temperature (25° C.) for 4 hrs. After the reaction is complete, add water (15 mL), extract with EtOAc (15 mL×2), combine the organic layers, wash with 1M HCl solution (15 mL) and brine (15 mL) sequentially, dry over anhydrous Na2SO4. Concentrate under reduced pressure to give a crude product (350 mg) which is used directly without further purification.

Workup

  1. extractionextract with EtOAc (15 mL×2)
  2. washwash with 1M HCl solution (15 mL) and brine (15 mL) sequentially
  3. dry with materialdry over anhydrous Na2SO4
  4. concentrationConcentrate under reduced pressure

Sources & evidence

ORD record
ord-60f1de8c6e8143a08a846b8d84ce3dff
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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