Triethylamine → HCID 53241215, compound

HRID 1505432Notes

Reaction equation

HRID 1505432 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([O:9][C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[NH2:19])=[CH:12][CH:11]=2)=[CH:5][C:4]=1[O:23][CH3:24])#[N:2].C(N(CC)CC)C.Cl[C:33]([O:36]C(=O)OC(Cl)(Cl)Cl)(Cl)Cl>C(Cl)Cl>[CH3:21][C:18]1([CH3:20])[C:17](=[O:22])[N:16]([C:13]2[CH:12]=[CH:11][C:10]([O:9][C:6]3[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[C:4]([O:23][CH3:24])[CH:5]=3)=[CH:15][CH:14]=2)[C:33](=[O:36])[NH:19]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 67235521HCID 67235521, compound2×

Product 1

HCID 53241215HCID 53241215, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

N1-(4-{[4-cyano-3-(methyloxy)phenyl]oxy}phenyl)-2-methylalaninamide (Intermediate 191, 77.0 mg) was dissolved in DCM (10 mL). Triethylamine (0.218 mL, 1.57 mmol) was added and the obtained mixture was cooled at 0° C. Bis(trichloromethyl)carbonate (68.1 mg, 0.22 mmol) was dissolved in 5 mL of DCM and the obtained solution was added dropwise to the reaction mixture. The reaction mixture was stirred at 0° C. After 15 min, the reaction mixture was evaporated in vacuo to obtain the crude product that was purified by silica gel chromatography (from 100:0 to 50:50 Cyclohexane/EtOAc in 10 CV; then 50:50 Cyclohexane/EtOAc for 10 CV) to obtain 65.1 mg of the title compound as a white solid

Workup

  1. additionthe obtained solution was added dropwise to the reaction mixture
  2. customthe reaction mixture was evaporated in vacuo
  3. customto obtain the crude product that
  4. customwas purified by silica gel chromatography (from 100:0 to 50:50 Cyclohexane/EtOAc in 10 CV

Sources & evidence

ORD record
ord-a6028fe37e3b4dfb8b9726509e9d3ba6
Source dataset
uspto-grants-2015_12
Patent number
US09216967B2

Reaction notes

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