N,O-Dimethylhydroxylamine → HCID 53645995, compound

HRID 1858103Notes

Reaction equation

HRID 1858103 reaction equation
[CH3:1][NH:2][O:3][CH3:4].[C:5]([O:9][C:10]([N:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]1[CH2:18][CH2:19][O:20][C:21]1[C:30]2[C:25](=[CH:26][C:27]([Cl:34])=[C:28]([C:31](O)=[O:32])[CH:29]=2)[NH:24][C:23](=[O:35])[C:22]=1[C:36]1[CH:41]=[C:40]([CH3:42])[CH:39]=[C:38]([CH3:43])[CH:37]=1)=[O:11])([CH3:8])([CH3:7])[CH3:6].Cl.CN(C)CCCN=C=NCC>CN(C)C1C=CN=CC=1.C(N(CC)CC)C>[C:5]([O:9][C:10]([N:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]1[CH2:18][CH2:19][O:20][C:21]1[C:30]2[C:25](=[CH:26][C:27]([Cl:34])=[C:28]([C:31](=[O:32])[N:2]([O:3][CH3:4])[CH3:1])[CH:29]=2)[NH:24][C:23](=[O:35])[C:22]=1[C:36]1[CH:37]=[C:38]([CH3:43])[CH:39]=[C:40]([CH3:42])[CH:41]=1)=[O:11])([CH3:6])([CH3:7])[CH3:8]

Participants

6

Reactant 3

HCID 14232N,O-DimethylhydroxylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22124479HCID 22124479, compound

Product 1

HCID 53645995HCID 53645995, compoundYield 81.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8471TriethylamineSolvent

Procedure

To a solution of N,O-dimethylhydroxylamine (1.14 g in 50 mL dry methylene chloride) was added 1.5 mL triethylamine followed by 4-[2-(1 -tert-butoxycarbonylpiperidin-2-yl)-ethoxy]-7-chloro-3-(3,5-dimethylphenyl)-2-oxo-1,2-dihydroquinoline-6-carboxylic acid (EXAMPLE 4.1, Step F, 1.35 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC, 1.35 g) and 4-dimethylaminopyridine (400 mg) and the mixture stirred at room temperature. After 36 hours, the mixture was concentrated in vacuo and the residue purified by flash chromatography on silica gel (ethyl acetate) to give the title compound (1.18 g).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customthe residue purified by flash chromatography on silica gel (ethyl acetate)

Sources & evidence

ORD record
ord-c51659a53cc0406b84bf69eb2a11af96
Source dataset
uspto-grants-2000_11
Patent number
US06150352

Reaction notes

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