m-Chloroperbenzoic acid → 6-(Tert-butoxycarbonyl)-2-chloro-5,6,7,8-tetrahydro-1,6-naphthyridine 1-oxide

HRID 2200068Notes

Reaction equation

HRID 2200068 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[Cl:12][C:13]1[CH:22]=[CH:21][C:20]2[CH2:19][N:18]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:17][CH2:16][C:15]=2[N:14]=1>C(Cl)(Cl)Cl>[C:26]([O:25][C:23]([N:18]1[CH2:17][CH2:16][C:15]2[N+:14]([O-:6])=[C:13]([Cl:12])[CH:22]=[CH:21][C:20]=2[CH2:19]1)=[O:24])([CH3:29])([CH3:28])[CH3:27]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 46835755tert-Butyl 2-chloro-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate

Product 1

HCID 866712756-(Tert-butoxycarbonyl)-2-chloro-5,6,7,8-tetrahydro-1,6-naphthyridine 1-oxideYield 56.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3-Chlorobenzoperoxoic acid (241 mg, 1.4 mmol) was added to a solution at 0° C. of tert-butyl 2-chloro-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate (250 mg, 0.93 mmol, see Example 1 procedure) in CHCl3 (3 mL). The reaction mixture thus obtained was warmed to room temperature and stirred overnight. After concentration, the residue was purified by flash chromatography on silica gel eluting with 0% to 80% EtOAc in hexane to give the title compound (150 mg, 56.6% yield). 1H NMR (400 MHz, CDCl3) δ ppm 1.51 (9H, s), 3.11 (2H, m), 3.77 (2H, t, J=6.16 Hz), 4.60 (2H, s), 6.99 (1H, d, J=8.41 Hz), 7.40 (1H, d, J=8.41 Hz) ppm; LC/MS m/z: 285 (M+1).

Workup

  1. customThe reaction mixture thus obtained
  2. concentrationAfter concentration
  3. customthe residue was purified by flash chromatography on silica gel eluting with 0% to 80% EtOAc in hexane

Sources & evidence

ORD record
ord-85b3be13927c4aeda971a7363d7b8511
Source dataset
uspto-grants-2016_06
Patent number
US09359355B2

Reaction notes

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