HCID 10776881, compound → HCID 131720681, compound

HRID 962943Notes

Reaction equation

[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:11][CH:12]=2)[CH:7]=[N:6]1.[IH:19].CS[C:22]1[NH:23][CH2:24][CH2:25][N:26]=1>N1C=CC=CC=1>[IH:19].[NH:26]1[CH2:25][CH2:24][N:23]=[C:22]1[NH:1][CH2:2][CH2:3][CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:11][CH:12]=2)[CH:7]=[N:6]1

Participants

Conditions

Temperature: 80 °C

Procedure

The crude product of Example 1198 Part A was combined with 2-methylthio-4,5-dihydroimidazole hydriodide (2.71 g, 11.1 mmol) and pyridine (125 mL), and the mixture was heated at 80° C. for 5 h. The mixture was allowed to cool to room temperature and concentrated under vacuum. The residue was purified by flash chromatography (dichloromethane:methanol 80:20) to provide the title product (3.73 g, 75%) as a gum: 1H NMR (DMSO-d6) δ 8.50 (s, 1H), 8.30 (s, 1H), 8.24 (bs, 1H), 7.98 (d, 1H), 7.75 (d, 1H), 4.49 (t, 2H), 4.34 (q, 2H), 3.57 (s, 4H), 3.13 (m, 2H), 2.05 (m, 2H), 1.35 (t, 3H); High resolution mass spectrum (NH3 --CI) calculated (M+H+) 316.1774, found 316.1765.

Workup

temperatureto cool to room temperature
concentrationconcentrated under vacuum
customThe residue was purified by flash chromatography (dichloromethane:methanol 80:20)

Sources & evidence

ORD record: ord-9603daff457b47959a53814605b2c301
Source dataset: uspto-grants-1998_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05760028

Reaction notes

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