Hydrochloric Acid → HCID 90020376, compound

HRID 2200193Notes

Reaction equation

HRID 2200193 reaction equation
CN1CCC(N[C:9]2[CH:14]=[C:13]([C:15]([F:18])([F:17])F)[CH:12]=[C:11]([NH2:19])[CH:10]=2)CC1.N1C=CC=C[CH:21]=1.Cl[C:27]([O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:28].Cl>C(Cl)Cl.O>[F:18][C:15]([C:13]1[CH:12]=[C:11]([NH:19][C:27](=[O:28])[O:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:10]=[CH:9][CH:14]=1)([F:17])[CH3:21]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 15891Phenyl chloroformateHCID 118223439HCID 118223439, compound

Product 1

HCID 90020376HCID 90020376, compoundYield 86.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
2.5 °C

Procedure

Dissolve the amine obtained in Step 2 (760 mg, 4.8 mmol) and pyridine (765 mg, 9.7 mmol) in DCM (15 mL) and cool to 0-5° C. on ice bath. Add dropwise phenyl chloroformate (831 mg, 5.3 mmol). After addition, stir the mixture at 0-5° C. for 2 hrs. Pour the mixture to water (50 mL), adjust pH to neutral with 1M HCl solution. Extract with EtOAc (15 mL×3), combine the organic layers and wash with brine (100 mL), dry over anhydrous Na2SO4. Concentrate under reduced pressure to give the crude product (1.15 g) which is used without further purification.

Workup

  1. additionAfter addition
  2. extractionExtract with EtOAc (15 mL×3)
  3. washwash with brine (100 mL)
  4. dry with materialdry over anhydrous Na2SO4
  5. concentrationConcentrate under reduced pressure

Sources & evidence

ORD record
ord-2fb55475ed6e494b8740a79950248026
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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