Dichloromethane → HCID 89589801, compound

HRID 2200859Notes

Reaction equation

HRID 2200859 reaction equation
ClC1[N:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([CH2:12][NH:13][CH3:14])=[C:5]2[NH:15][CH:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]1.Cl[C:30](Cl)([O:32]C(=O)OC(Cl)(Cl)Cl)Cl.C(N(CC)CC)C.[CH2:48]([Cl:50])Cl>>[Cl:50][C:48]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[CH2:12][N:13]([CH3:14])[C:30](=[O:32])[N:15]([CH:16]4[CH2:17][CH2:18][N:19]([C:22]([O:24][C:25]([CH3:26])([CH3:28])[CH3:27])=[O:23])[CH2:20][CH2:21]4)[C:5]=3[C:4]=2[N:3]=1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 94429TriphosgeneHCID 90449279HCID 90449279, compound

Product 1

HCID 89589801HCID 89589801, compound

Procedure

In DCM (10 mL) was dissolved tert-butyl 4-((6-chloro-3-((methylamino)methyl)-1,5-naphthyridin-4-yl)amino)piperidine-1-carboxylate (0.312 g, 0.77 mmol). The solution was cooled in an ice bath, and triphosgene (0.274 g, 0.923 mmol) and triethylamine (0.324 mL) were added. Then the reaction mixture was stirred at ambient temperature for 2 h. The reaction was quenched with saturated aqueous sodium carbonate and extracted with DCM. The organic phase was dried over sodium sulfate. The solvent was removed under reduced pressure to give a solid (0.332 g), which was used in the subsequent procedure without further purification.

Workup

  1. temperatureThe solution was cooled in an ice bath
  2. customThe reaction was quenched with saturated aqueous sodium carbonate
  3. extractionextracted with DCM
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-a610627992e14854a7924b1c593ed0ab
Source dataset
uspto-grants-2016_06
Patent number
US09359371B2

Reaction notes

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