Methanesulfonyl chloride → HCID 58124794, compound

HRID 1971763Notes

Reaction equation

HRID 1971763 reaction equation
[C:1]([N:5]1[CH2:31][CH2:30][CH2:29][CH2:28][C:8]2[C:9]([C:23]3[S:24][CH:25]=[CH:26][CH:27]=3)=[C:10]3[C:19]4[CH:18]=[C:17]([NH2:20])[C:16]([O:21][CH3:22])=[CH:15][C:14]=4[CH2:13][CH2:12][N:11]3[C:7]=2[C:6]1=[O:32])([CH3:4])([CH3:3])[CH3:2].[CH3:33][S:34](Cl)(=[O:36])=[O:35].C(N(CC)C(C)C)(C)C>C(Cl)Cl>[C:1]([N:5]1[CH2:31][CH2:30][CH2:29][CH2:28][C:8]2[C:9]([C:23]3[S:24][CH:25]=[CH:26][CH:27]=3)=[C:10]3[C:19]4[CH:18]=[C:17]([NH:20][S:34]([CH3:33])(=[O:36])=[O:35])[C:16]([O:21][CH3:22])=[CH:15][C:14]=4[CH2:13][CH2:12][N:11]3[C:7]=2[C:6]1=[O:32])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 58124894HCID 58124894, compound

Product 1

HCID 58124794HCID 58124794, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 12.5 mg 20b in 2 mL methylene chloride was added 3.2 μL methanesulphonyl chloride and 9.2 μL N,N-diisopropylethylamine. The mixture was stirred at room temperature. After 1 h the mixture was diluted with methylene chloride and was washed with water. The organic phase was dried and concentrated. The crude product was purified by preparative HPLC on a reversed phase C18 column to give 1.8 mg of compound 29a.

Workup

  1. washwas washed with water
  2. customThe organic phase was dried
  3. concentrationconcentrated
  4. customThe crude product was purified by preparative HPLC on a reversed phase C18 column

Sources & evidence

ORD record
ord-6173e6e5c9274db7b414c3244f838704
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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