Benzyl chloroformate → HCID 86726879, compound

HRID 924421Notes

Reaction equation

HRID 924421 reaction equation
[NH2:1][C:2]1[C:3]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([O:12][CH2:13][CH3:14])[N:6]=2.CCN(C(C)C)C(C)C.Cl[C:30]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31]>C(Cl)Cl>[CH2:33]([O:32][C:30]([NH:1][C:2]1[C:3]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([O:12][CH2:13][CH3:14])[N:6]=2)=[O:31])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 86726878HCID 86726878, compound

Product 1

HCID 86726879HCID 86726879, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of ethyl 3-amino-7-ethoxy-1,8-naphthyridine-2-carboxylate (51 mg, 0.20 mmol) and DIPEA (100 μL, 0.58 mmol) in DCM (0.7 mL), benzyl chloroformate (84 μL, 0.58 mmol) was added and the reaction mixture was heated at 65° C. with stirring in a sealed vial for 16 h. The crude reaction mixture was concentrated under reduced pressure and the residue was purified by flash chromatography (24 g silica gel column, eluting with 0-40% EtOAc/hexanes) to afford the sub-title compound. LCMS (ESI) calc. for C21H22N3O5 [M+H]+: m/z=396.2. found: 396.1.

Workup

  1. customThe crude reaction mixture
  2. concentrationwas concentrated under reduced pressure
  3. customthe residue was purified by flash chromatography (24 g silica gel column, eluting with 0-40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-5c4cb02907c3499cbcbb58f4433bd9bc
Source dataset
uspto-grants-2016_03
Patent number
US09278950B2

Reaction notes

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