Dichloromethane → HCID 89589801, compound

HRID 925516Notes

Reaction equation

HRID 925516 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.Cl[CH2:49][Cl:50]>>[Cl:50][C:49]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

tert-butyl 4-((6-chloro-3-((methylamino)methyl)-1,5-naphthyridin-4-yl)amino)piperidine-1-carboxylate (0.312 g, 0.77 mmol) was dissolved in dichloromethane (10 mL), to the reaction flask in an ice bath added triphosgene (0.274 g, 0.923 mmol) and triethylamine (0.324 mL). The mixture was stirred at room temperature for 2 h. The reaction was quenched with a saturated aqueous solution of sodium carbonate, and extracted with 80 mL of dichloromethane. The organic layer was dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure to give 0.332 g of a solid. The solid was used directly in the next step.

Workup

  1. customThe reaction was quenched with a saturated aqueous solution of sodium carbonate
  2. extractionextracted with 80 mL of dichloromethane
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-f4d7f1b1a1c6444b906b12006c912088
Source dataset
uspto-grants-2016_03
Patent number
US09284315B2

Reaction notes

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