Triethylamine → HCID 178490681, compound

HRID 556684Notes

Reaction equation

HRID 556684 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[CH:8]=[C:7]([C:9]([CH3:12])([CH3:11])[CH3:10])[S:6]/[C:5]/1=[N:13]\[C:14](=[O:24])[C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=1[O:22][CH3:23].[CH3:25][S:26](Cl)(=[O:28])=[O:27].C(N(CC)CC)C>O1CCCC1.C(OCC)(=O)C>[C:9]([C:7]1[S:6]/[C:5](=[N:13]\[C:14](=[O:24])[C:15]2[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=2[O:22][CH3:23])/[N:4]([CH2:3][CH2:2][NH:1][S:26]([CH3:25])(=[O:28])=[O:27])[CH:8]=1)([CH3:11])([CH3:12])[CH3:10]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 178490679HCID 178490679, compound

Product 1

HCID 178490681HCID 178490681, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of Example 12A (0.29 g, 0.79 mmol) in tetrahydrofuran (10 mL) was treated with methanesulfonyl chloride (0.6 mL, 0.79 mmol) and triethylamine (0.33 mL, 0.24 mmol) and stirred at room temperature for 1 hour. The mixture was diluted with ethyl acetate, washed with water, brine, dried with MgSO4, filtered, and concentrated. The residue was purified by flash chromatography (SiO2, eluting with a gradient from 0 to 100% ethyl acetate in hexane over 600 mL then isocratic for 300 mL) to provide the title compound (0.28 g, 0.63 mMol, 80% yield). MS (DCI/NH3) m/z 446.1 (M+H)+. 1H NMR (300 MHz, CDCl3) δ ppm 1.36 (s, 9H) 2.78 (s, 3H) 3.62 (ddd, J=6.94, 5.55, 4.16 Hz, 2H) 3.92 (s, 3H) 4.33-4.39 (m, 2H) 5.80 (t, J=5.35 Hz, 1H) 6.70 (s, 1H) 6.93 (d, J=9.12 Hz, 1H) 7.35 (dd, J=9.12, 2.78 Hz, 1H) 7.89 (d, J=2.78 Hz, 1H).

Workup

  1. washwashed with water, brine
  2. dry with materialdried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (SiO2
  6. washeluting with a gradient from 0 to 100% ethyl acetate in hexane over 600 mL

Sources & evidence

ORD record
ord-da2232ed510d41daaa19d8521a2b4674
Source dataset
uspto-grants-2011_11
Patent number
US08058293B2

Reaction notes

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