Pyridine → HCID 118223422, compound

HRID 2200175Notes

Reaction equation

HRID 2200175 reaction equation
[CH3:1][N:2]1[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)[CH2:4][CH2:3]1.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].C(Cl)Cl>C1COCC1.O.CCOC(C)=O.CO>[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([NH:8][C:9]2[CH:10]=[C:11]([NH:19][C:27](=[O:28])[O:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH:12]=[C:13]([C:15]([F:16])([F:17])[F:18])[CH:14]=2)[CH2:4][CH2:3]1

Participants

9

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 15891Phenyl chloroformateHCID 118223439HCID 118223439, compound

Product 1

HCID 118223422HCID 118223422, compoundYield 103%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-30 °C

Procedure

Dissolve the compound obtained in Step 2 (2.9 g, 10.61 mmol) in THF (30 mL), cool to −30° C., then add pyridine (1.68 g, 21.22 mmol) and phenyl chloroformate (1.83 g, 11.67 mmol). Stir at room temperature for 3 hrs. TLC (DCM:MeOH=10:1) shows the reaction is complete. Pour the solution to a mixture of EtOAc and water, separate the organic layer, and wash with brine, dry over anhydrous Na2SO4. Concentrate under reduced pressure to give the crude product (4.3 g). MS: (M+1): 394.1.

Workup

  1. additionPour the solution
  2. customseparate the organic layer
  3. washwash with brine
  4. dry with materialdry over anhydrous Na2SO4
  5. concentrationConcentrate under reduced pressure

Sources & evidence

ORD record
ord-2bba873f37c442c59a339052939fd9ee
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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