2,5-Dimethoxytetrahydrofuran → HCID 131728518, compound

HRID 1172552Notes

Reaction equation

CO[CH:3]1[CH2:7][CH2:6][CH:5](OC)O1.[CH3:10][O:11][C:12]([C:14]1[CH:15]=[C:16]([CH3:34])[C:17]2[O:23][C:22]3[C:24]([Cl:30])=[CH:25][C:26]([CH2:28][NH2:29])=[CH:27][C:21]=3[CH2:20][S:19](=[O:32])(=[O:31])[C:18]=2[CH:33]=1)=[O:13].Cl.ClC1C=CN=CC=1>O1CCOCC1>[CH3:10][O:11][C:12]([C:14]1[CH:15]=[C:16]([CH3:34])[C:17]2[O:23][C:22]3[C:24]([Cl:30])=[CH:25][C:26]([CH2:28][N:29]4[CH:3]=[CH:7][CH:6]=[CH:5]4)=[CH:27][C:21]=3[CH2:20][S:19](=[O:31])(=[O:32])[C:18]=2[CH:33]=1)=[O:13]

Participants

Conditions

Temperature: 110 °C

Procedure

2,5-Dimethoxytetrahydrofuran (0.090 mL, 0.655 mmol) was added with stirring to a solution of Example 198k (0.2 g, 0.52 mmol) in dry dioxane (10 mL) followed by the addition of 4-chloropyridine hydrochloride (0.008 g, 0.05 mmol). The reaction mixture was allowed to stir at 110° C. for 2 h under nitrogen atmosphere. It was concentrated, treated with cold water and the solid that precipitated was filtered, washed with water, dried and purified using flash chromatography (silica gel, chloroform/pet ether) to obtain the title compound as a white solid. Yield: 0.086 g, (41.54%); 1H NMR (DMSO-d6): δ 2.69 (s, 3H, CH3), 3.92 (s, 3H, OCH3), 4.67 (s, 2H, CH2), 5.02 (s, 2H, CH2), 6.22 (s, 2H, Ar), 6.68 (s, 2H, Ar), 7.04 (s, 1H, Ar), 7.38 (s, 1H, Ar), 8.09 (s, 1H, Ar), 8.46 (s, 1H, Ar); MS: m/e (ES+) 432 (M+1).

Workup

concentrationIt was concentrated
additiontreated with cold water
customthe solid that precipitated
filtrationwas filtered
washwashed with water
customdried
custompurified

Sources & evidence

ORD record: ord-96d443a82fd44d2cb35291399ac60365
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07834001B2

Reaction notes

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