Benzyl chloroformate → HCID 86726883, compound

HRID 924432Notes

Reaction equation

HRID 924432 reaction equation
[NH2:1][C:2]1[C:3]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][N:8]=[C:7]([Br:12])[CH:6]=2.CCN(C(C)C)C(C)C.Cl[C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29]>C(Cl)Cl>[CH2:31]([O:30][C:28]([NH:1][C:2]1[C:3]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][N:8]=[C:7]([Br:12])[CH:6]=2)=[O:29])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 86726882HCID 86726882, compound

Product 1

HCID 86726883HCID 86726883, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of ethyl 3-amino-7-bromo-1,6-naphthyridine-2-carboxylate (47 mg, 0.16 mmol) and DIPEA (83 μL, 0.48 mmol) in DCM (1.5 mL), a solution of benzyl chloroformate (68 μL, 0.48 mmol) was added and the resulting mixture was heated at 60° C. in a sealed vial for 14 h. The crude reaction mixture was then concentrated under reduced pressure and the residue was purified by flash chromatography (24 g silica gel column, eluting with 0-60% EtOAc/hexanes) to afford the sub-title compound (41 mg, 60%). LCMS (ESI) calc. for C19H17BrN3O4[M+H]+: m/z=430.0. found: 429.9.

Workup

  1. customThe crude reaction mixture
  2. concentrationwas then concentrated under reduced pressure
  3. customthe residue was purified by flash chromatography (24 g silica gel column, eluting with 0-60% EtOAc/hexanes)

Sources & evidence

ORD record
ord-9f1127c387884f36ab19e6e1c3e617c4
Source dataset
uspto-grants-2016_03
Patent number
US09278950B2

Reaction notes

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