Hydrochloric Acid → HCID 118223421, compound

HRID 2200178Notes

Reaction equation

HRID 2200178 reaction equation
CN1[CH2:7][CH2:6][CH:5]([NH:8][C:9]2[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[C:11]([NH2:19])[CH:10]=2)CC1.N1C=CC=CC=1.Cl[C:27]([O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:28].Cl.[OH2:37]>C(Cl)Cl>[C:5]([NH:8][C:9]1[CH:10]=[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:12]=[C:13]([C:15]([F:16])([F:17])[F:18])[CH:14]=1)(=[O:37])[CH:6]=[CH2:7]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 1049PyridineHCID 15891Phenyl chloroformateHCID 118223439HCID 118223439, compound

Product 1

HCID 118223421HCID 118223421, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve the product obtained in Step 2 (168 mg, 0.73 mmol) in DCM (6 mL), add pyridine (115 mg, 1.46 mmol) and then cool to 0° C. on ice bath. Add slowly phenyl chloroformate (125 mg, 0.8 mmol), stir at 0-5° C. for 2 hrs. Pour the mixture into water (50 mL), adjust pH to neutral with 1M HCl and extract with EtOAc (15 mL×3). Combine the organic layers, wash with brine (100 mL) and dry over anhydrous Na2SO4. Concentrate under reduced pressure to give the crude product (240 mg) which is used without further purification.

Workup

  1. extractionextract with EtOAc (15 mL×3)
  2. washCombine the organic layers, wash with brine (100 mL)
  3. dry with materialdry over anhydrous Na2SO4
  4. concentrationConcentrate under reduced pressure

Sources & evidence

ORD record
ord-ecefeb36e46241a19477cf6a334f2158
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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