Methyl iodide → HCID 135955740, compound

HRID 731335Notes

Reaction equation

HRID 731335 reaction equation
[CH3:1][C:2]([CH3:37])([CH3:36])[CH2:3][CH2:4][N:5]1[C:10](=[O:11])[C:9]([C:12]2[NH:17][C:16]3[CH:18]=[CH:19][C:20]([NH:22][S:23]([CH3:26])(=[O:25])=[O:24])=[CH:21][C:15]=3[S:14](=[O:28])(=[O:27])[N:13]=2)=[C:8]([OH:29])[CH:7]2[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH:6]12.[C:38](=O)([O-])[O-].[K+].[K+].IC>CN(C)C=O>[CH3:1][C:2]([CH3:37])([CH3:36])[CH2:3][CH2:4][N:5]1[C:10](=[O:11])[C:9]([C:12]2[NH:17][C:16]3[CH:18]=[CH:19][C:20]([N:22]([CH3:38])[S:23]([CH3:26])(=[O:24])=[O:25])=[CH:21][C:15]=3[S:14](=[O:28])(=[O:27])[N:13]=2)=[C:8]([OH:29])[CH:7]2[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH:6]12

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 135955714HCID 135955714, compound

Product 1

HCID 135955740HCID 135955740, compoundYield 63.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

N-{3-[1-(3,3-Dimethyl-butyl)-4-hydroxy-2-oxo-1,2,4a,5,6,7,8,9,10,10a-decahydro-cycloocta[b]pyridin-3-yl]-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl}-methanesulfonamide (prepared as described in Example 35b, 0.20 g, 0.36 mmol) was dissolved in N,N-dimethylformamide (12 mL). Potassium carbonate (0.10 g, 0.72 mmol) and iodomethane (0.025 mL, 0.40 mmol) were added sequentially. The reaction was stirred at 25° C. for 3 h. The reaction was quenched via the addition of 1.0 M aqueous hydrochloric acid solution (20 mL). The mixture was extracted with ethyl acetate (3×30 mL). The organic layers were combined and washed with saturated aqueous brine solution (20 mL) before they were dried over magnesium sulfate, filtered, and concentrated in vacuo to afford a golden oil. Purification by flash column chromatography (Teledyne Isco RediSep Flash Column 12 g; 0-20% ethyl acetate in dichloromethane) afforded the desired product, N-{3-[1-(3,3-dimethyl-butyl)-4-hydroxy-2-oxo-1,2,4a,5,6,7,8,9,10,10a-decahydro-cycloocta[b]pyridin-3-yl]-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl}-N-methyl-methanesulfonamide (0.018 g, 0.23 mmol, 9%), as a white powder. 1H NMR (400 MHz, DMSO-d6) δ: 1.00-1.02 (9H, m), 1.35-1.80 (14H, m), 2.87-2.88 (3H, m), 3.00-3.35 (2H, m), 3.36-3.38 (3H, m), 3.86-4.15 (2H, m), 7.20-7.28 (1H, m), 7.64-7.79 (2H, m). LC-MS (ESI) calcd for C26H38N4O6S2 566.73, found 567.4 [M+H+].

Workup

  1. customThe reaction was quenched via the addition of 1.0 M aqueous hydrochloric acid solution (20 mL)
  2. extractionThe mixture was extracted with ethyl acetate (3×30 mL)
  3. washwashed with saturated aqueous brine solution (20 mL) before they
  4. dry with materialwere dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto afford a golden oil
  8. customPurification by flash column chromatography (Teledyne Isco RediSep Flash Column 12 g; 0-20% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-b512b55c79a34221979dba0a43e928d7
Source dataset
uspto-grants-2009_09
Patent number
US07582626B2

Reaction notes

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