Methanesulfonyl chloride → HCID 68194838, compound

HRID 2370645Notes

Reaction equation

HRID 2370645 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[C:14](=[O:15])[C:13]2[CH:16]=[N:17][C:18]([NH:20][C:21]3[CH:30]=[C:29]4[C:24]([C:25]5([CH2:32][CH2:31]5)[CH2:26][NH:27][CH2:28]4)=[CH:23][CH:22]=3)=[N:19][C:12]=2[N:11]2[CH:33]=[CH:34][N:35]=[C:10]12.C(N(C(C)C)CC)(C)C.[CH3:45][S:46](Cl)(=[O:48])=[O:47]>CN(C)C=O.C(OCC)(=O)C>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[N:9]1[C:14](=[O:15])[C:13]2[CH:16]=[N:17][C:18]([NH:20][C:21]3[CH:30]=[C:29]4[C:24]([C:25]5([CH2:31][CH2:32]5)[CH2:26][N:27]([S:46]([CH3:45])(=[O:48])=[O:47])[CH2:28]4)=[CH:23][CH:22]=3)=[N:19][C:12]=2[N:11]2[CH:33]=[CH:34][N:35]=[C:10]12

Participants

6

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 68195150HCID 68195150, compound

Product 1

HCID 68194838HCID 68194838, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of Example 109B (75 mg, 0.149 mmol) in 2 mL N,N-dimethylformamide was added diisopropylethylamine (0.130 ml, 0.744 mmol) followed by methanesulfonyl chloride (0.017 ml, 0.223 mmol). The reaction mixture was stirred at room temperature overnight, then diluted with ethyl acetate. The organics were washed with saturated aqueous NaHCO3, water, and brine, dried over MgSO4, filtered, and concentrated. The crude material was triturated with ethyl acetate, filtered and dried over high vacuum to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ 0.85-1.12 (m, 4H) 1.99 (s, 2H) 2.86-3.02 (m, 3H) 4.55 (s, 2H) 6.90 (d, J=8.33 Hz, 1H) 7.13 (d, J=1.59 Hz, 1H) 7.44-7.94 (m, 6H) 9.16 (s, 1H) 10.84 (s, 1H). MS (ESI+) m/z 582.1 (M+H)+.

Workup

  1. washThe organics were washed with saturated aqueous NaHCO3, water, and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude material was triturated with ethyl acetate
  6. filtrationfiltered
  7. customdried over high vacuum

Sources & evidence

ORD record
ord-d0671e320b74493fbcdac5490ad90fdb
Source dataset
uspto-grants-2014_04
Patent number
US08710065B2

Reaction notes

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