Dimethyl Sulfoxide → HCID 69745485, compound

HRID 1760044Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].F[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N+:14]([O-:16])=[O:15].CS(C)=O.Cl.[NH2:22][CH:23]([C:40]([CH3:43])([CH3:42])[CH3:41])[C:24]([N:26]1[CH2:35][CH2:34][C:33]2[C:28](=[CH:29][C:30]([O:38][CH3:39])=[C:31]([O:36][CH3:37])[CH:32]=2)[CH2:27]1)=[O:25]>C(OCC)C>[CH3:37][O:36][C:31]1[CH:32]=[C:33]2[C:28](=[CH:29][C:30]=1[O:38][CH3:39])[CH2:27][N:26]([C:24](=[O:25])[C@@H:23]([NH:22][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N+:14]([O-:16])=[O:15])[C:40]([CH3:41])([CH3:43])[CH3:42])[CH2:35][CH2:34]2

Participants

Conditions

Temperature: 80 °C

Procedure

Anhydrous potassium carbonate (640 mg, 4.63 mmol) and 2-fluoronitrobenzene (820 mg, 5.81 mmol) were added to a dimethyl sulfoxide (100 ml) solution of N-(2-amino-3,3-dimethylbutyryl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (1.05 g, 3.42 mmol) obtained in Reference example 7, and the mixture was heated at 80° C. for 90 minutes. The reaction mixture was cooled to room temperature, diluted with a diethyl ether solution (200 ml), washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography using ethyl acetate and hexane (1:4 to 2:1) as an eluent to obtain the captioned compound (395 mg, 27%) as an orange foamy substance.

Workup

customobtained in Reference example 7
temperatureThe reaction mixture was cooled to room temperature
washwashed with water
dry with materialdried over anhydrous magnesium sulfate
distillationthe solvent was distilled off under reduced pressure
customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-40ed47afac5b49fdaf959051f95f3ee6
Source dataset: uspto-grants-2005_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06838465B2

Reaction notes

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