Methyl chloroformate → HCID 86612782, compound

HRID 2364367Notes

Reaction equation

HRID 2364367 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[C:14]2[C:9](=[N:10][CH:11]=[C:12]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[CH:13]=2)[C:8]([OH:23])=[C:7]([C:24]([NH:26][CH2:27][CH2:28][O:29][CH2:30][CH3:31])=[O:25])[C:6]1=[O:32].Cl[C:34]([O:36][CH3:37])=[O:35].C(N(C(C)C)CC)(C)C>CN(C=O)C>[CH2:30]([O:29][CH2:28][CH2:27][NH:26][C:24]([C:7]1[C:6](=[O:32])[N:5]([CH2:4][CH2:3][CH2:2][NH:1][C:34](=[O:35])[O:36][CH3:37])[C:14]2[C:9]([C:8]=1[OH:23])=[N:10][CH:11]=[C:12]([CH2:15][C:16]1[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=1)[CH:13]=2)=[O:25])[CH3:31]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 69481020HCID 69481020, compound

Product 1

HCID 86612782HCID 86612782, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(3-aminopropyl)-N-[2-(ethyloxy)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (15 mg, 0.034 mmol), methyl chloroformate (2.6 μL, 034 mmol) and diisopropylethyl amine (30 μL, 0.17 mmol) in anhydrous DMF (1.5 mL) was stirred under nitrogen at ambient temperature overnight. The crude reaction mixture was evaporated in vacuo and purified by reverse phase chromatography eluting with 10-90% aqueous CH3CN containing 0.1% formic acid to provide the product as a white solid: 1H NMR (CDCl3) δ 10.29 (2H, b), 8.57 (1H, s), 7.36 (1H, s), 7.13-7.18 (2H, m), 7.00-7.05 (2H, m), 5.60 (2H, b), 4.23 (2H, t, J=7 Hz), 4.13 (2H, s), 3.67 (3H, s), 3.63 (2H, b), 3.56 (2H, q, J=7 Hz), 3.11 (2H, b), 1.74-1.81 (2H, m), 1.24 (3H, t, J=7 Hz); ES+ MS: 501 (M+H+).

Workup

  1. customThe crude reaction mixture
  2. customwas evaporated in vacuo
  3. custompurified by reverse phase chromatography
  4. washeluting with 10-90% aqueous CH3CN containing 0.1% formic acid

Sources & evidence

ORD record
ord-422f36c7b1ac4b64afda4d20c0214a06
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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