Methyl iodide → HCID 42646741, compound

HRID 1724664Notes

Reaction equation

[OH:1][C:2]1[C:3]2[CH:27]=[CH:26][S:25][C:4]=2[N:5]([CH:22]([CH3:24])[CH3:23])[C:6](=[O:21])[C:7]=1[C:8]([NH:10][CH2:11][CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][CH:17](C)[CH2:16][CH2:15]1)=[O:9].[CH2:28]([Li])CCC.CI>C1COCC1>[CH:22]([N:5]1[C:6](=[O:21])[C:7]([C:8]([NH:10][CH2:11][CH2:12][CH2:13][N:14]2[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]2)=[O:9])=[C:2]([O:1][CH3:28])[C:3]2[CH:27]=[CH:26][S:25][C:4]1=2)([CH3:24])[CH3:23]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 6,7-dihydro-4-hydroxy-7-isopropyl-N-(3-(4-methylpiperidin-1-yl)propyl)-6-oxothieno[2,3-b]pyridine-5-carboxamide (0.075 g, 0.20 mmol) in THF (2.5 mL) at −78° C. was added n-butyllithium (0.087 mL, 2.5 M in hexanes, 0.22 mmol). The reaction mixture was warmed to 0° C. for 30 min and re-cooled to −78° C.; then methyl iodide (0.037 mL, 0.40 mmol) was added. The mixture was warmed to room temperature, stirred for 4 h and concentrated. The residue was dissolved in dichloromethane; the resulting solution was washed with water, dried over anhydrous sodium sulfate and concentrated to afford the title compound as an off-white solid (0.077 g, 99%). 1H NMR (400 MHz, CD3OD): δ 7.35 (d, 1 H), 7.20 (d, 1 H), 3.55 (t, 2 H), 3.49-3.45 (m, 2 H), 3.40 (t, 4 H), 3.09 (s, 3 H), 2.17-2.09 (m, 2 H), 1.91 (m, 4 H), 1.76-1.62 (m, 2 H), 1.64 (d, 6 H); MS: m/e 392 (M+H+).

Workup

temperaturere-cooled to −78° C.
temperatureThe mixture was warmed to room temperature
concentrationconcentrated
dissolutionThe residue was dissolved in dichloromethane
washthe resulting solution was washed with water
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-0c6578e1b46846e9af71aa07eee4a203
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07488736B2

Reaction notes

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