Methanesulfonyl chloride → HCID 87191905, compound

HRID 2089000Notes

Reaction equation

HRID 2089000 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:5]=[C:4]([C:15]2[C:23]3[C:18](=[N:19][CH:20]=[CH:21][CH:22]=3)[NH:17][CH:16]=2)[CH:3]=1.C(N(C(C)C)CC)(C)C.[CH3:33][S:34](Cl)(=[O:36])=[O:35]>C1COCC1.C(OCC)(=O)C>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH:9]2[CH2:14][CH2:13][N:12]([S:34]([CH3:33])(=[O:36])=[O:35])[CH2:11][CH2:10]2)[CH:5]=[C:4]([C:15]2[C:23]3[C:18](=[N:19][CH:20]=[CH:21][CH:22]=3)[NH:17][CH:16]=2)[CH:3]=1

Participants

6

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 87191894HCID 87191894, compound

Product 1

HCID 87191905HCID 87191905, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of Example 33 (0.04 g, 0.095 mmol) in 2 mL anhydrous THF was added diisopropylethylamine (0.07 mL, 0.38 mmol) followed by methanesulfonyl chloride (0.009 mL, 0.114 mmol). The resulting solution was stirred at room temperature for 2.5 hours. The reaction mixture was diluted with ethyl acetate and washed with water, brine, dried over magnesium sulfate, filtered, and concentrated to give the title compound as an off-white solid. 1H NMR (300 MHz, DMSO-d6) ppm 1.16-1.35 (m, 1H) 1.38-1.61 (m, 3H) 1.93-2.10 (m, 3H) 2.90-3.04 (m, 2H) 3.52 (d, J=12.21 Hz, 2H) 3.84 (s, 1H) 6.82-7.00 (m, 3H) 7.21 (dd, J=7.80, 5.09 Hz, 1H) 8.14 (d, J=3.05 Hz, 1H) 8.24-8.37 (m, 2H) 12.16 (s, 1H). MS (ESI+) m/z 406.0 (M+H)+.

Workup

  1. washwashed with water, brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5f49150ffa5342fdb9afd94fe20a0685
Source dataset
uspto-grants-2013_05
Patent number
US08435980B2

Reaction notes

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