Methanesulfonyl chloride → HCID 71610198, compound

HRID 1479056Notes

Reaction equation

HRID 1479056 reaction equation
[Cl:1][C:2]1[C:10]([CH3:11])=[N:9][C:8]2[N:4]([N:5]=[C:6]3[CH2:14][N:13]([C:15]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=4[O:23][CH:24]4[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]4)=[O:16])[CH2:12][C:7]3=2)[C:3]=1[CH3:30].[CH3:31][S:32](Cl)(=[O:34])=[O:33]>C(Cl)Cl>[Cl:1][C:2]1[C:10]([CH3:11])=[N:9][C:8]2[N:4]([N:5]=[C:6]3[CH2:14][N:13]([C:15]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=4[O:23][CH:24]4[CH2:29][CH2:28][N:27]([S:32]([CH3:31])(=[O:34])=[O:33])[CH2:26][CH2:25]4)=[O:16])[CH2:12][C:7]3=2)[C:3]=1[CH3:30]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 71610126HCID 71610126, compound

Product 1

HCID 71610198HCID 71610198, compoundYield 36.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of Example 3 (100 mg; 0.23 mmol; 1 eq.) and TEA (82 μL; 0.59 mmol; 2.5 eq.) in DCM (3 mL) at 0° C. was added methanesulfonyl chloride (22 μL; 0.28 mmol; 1.2 eq.). The reaction mixture was stirred at room temperature for 16 hours. The solution was diluted with DCM, washed successively with 0.1M HCl and brine, dried over magnesium sulfate and concentrated in vacuo. Purification by mass directed preparative HPLC afforded the title compound (42 mg, 35%) as a white solid. 1H NMR (CDCl3) δ 7.43-7.34 (m, 2H), 7.12-7.05 (m, 1H), 7.01-6.96 (m, 1H), 4.98 (s, 0.7H), 4.97 (s, 1.3H), 4.69-4.64 (m, 3H), 3.39-3.32 (m, 2H), 3.18-3.08 (m, 2H), 2.91 (s, 2H), 2.86 (s, 1H), 2.72 (s, 3H), 2.70 (s, 1H), 2.62 (s, 2H), 2.00-1.93 (m, 4H). HPLC (max plot) 98.0%, Rt 3.61 min. UPLC/MS: (MS+) 504.4 ([M+H]+).

Workup

  1. washwashed successively with 0.1M HCl and brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customPurification by mass

Sources & evidence

ORD record
ord-3688142a4ce345629737f3c35f9d1056
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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