Pyridine → HCID 90027934, compound

HRID 2200190Notes

Reaction equation

HRID 2200190 reaction equation
CN1CCC([NH:8][C:9]2C=[C:11]([NH:19][C:20](=[O:28])[O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:12]=[C:13]([C:15]([F:18])([F:17])F)[CH:14]=2)CC1.N1C=CC=C[CH:30]=1.ClC(OC1C=CC=CC=1)=O>C(Cl)Cl>[F:18][C:15]([C:13]1[CH:14]=[CH:9][N:8]=[C:11]([NH:19][C:20](=[O:28])[O:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:12]=1)([F:17])[CH3:30]

Participants

5

Reactant 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 118223422HCID 118223422, compound

Product 1

HCID 90027934HCID 90027934, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Add the amine obtained in Step 3 (624 mg, 3.95 mmol), pyridine (780 mg, 9.85 mmol) in DCM (15 mL), cool to 0° C. on ice bath. Add slowly a solution of phenyl chloroformate (678 mg, 4.34 mmol) in DCM. After addition, stir on ice bath for 1 hr. Concentrate the mixture to get a crude residue. Purification by chromatography (silica gel, EtOAc:PE=1:3) affords the target compound (780 mg, 71%). MS: (M+1): 279.1.

Workup

  1. additionAfter addition
  2. concentrationConcentrate the mixture
  3. customto get a crude residue
  4. customPurification by chromatography (silica gel, EtOAc:PE=1:3)

Sources & evidence

ORD record
ord-14faf7606b45424797c24307b7f57000
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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