Methanesulfonyl chloride → HCID 46832634, compound

HRID 1848365Notes

Reaction equation

HRID 1848365 reaction equation
[OH:1][CH2:2][C:3]1([C:6]2[N:24]=[C:9]3[C:10]([O:22][CH3:23])=[CH:11][CH:12]=[C:13]([C:14]4[CH:15]=[N:16][CH:17]=[C:18]([CH:21]=4)[C:19]#[N:20])[N:8]3[N:7]=2)[CH2:5][CH2:4]1.[CH3:25]S(Cl)(=O)=O.CCN([CH:36]([CH3:38])[CH3:37])C(C)C>C(Cl)Cl>[CH2:37]([O:1][CH2:2][C:3]1([C:6]2[N:24]=[C:9]3[C:10]([O:22][CH3:23])=[CH:11][CH:12]=[C:13]([C:14]4[CH:15]=[N:16][CH:17]=[C:18]([CH:21]=4)[C:19]#[N:20])[N:8]3[N:7]=2)[CH2:4][CH2:5]1)[CH:36]([CH3:38])[CH3:25]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 58074628HCID 58074628, compound

Product 1

HCID 46832634HCID 46832634, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 248 (0.02 g, 0.06 mmol) was dissolved in DCM (2 mL). TEA (0.035 mL, 0.25 mmol) and methanesulfonyl chloride (0.007 mL, 0.09 mmol) were added and stirred under argon for 30 min. The reaction mixture was washed with H2O and the organic phase was filtered through a phase separation cartridge (chromabond PTS). The solvent was concentrated and the crude product was suspended in iso-butanol (6 mL) under an argon atmosphere. DIPEA (0.05 mL, 0.31 mmol) was added and the mixture was stirred at 60° C. for 18 h. Iso-butanol was evaporated and the crude product was purified by preparative HPLC/MS to afford the title compound.

Workup

  1. washThe reaction mixture was washed with H2O
  2. filtrationthe organic phase was filtered through a phase separation cartridge (chromabond PTS)
  3. concentrationThe solvent was concentrated
  4. stirringthe mixture was stirred at 60° C. for 18 h
  5. customIso-butanol was evaporated
  6. customthe crude product was purified by preparative HPLC/MS

Sources & evidence

ORD record
ord-cead62b2328b4a0e880f3ba993b889fa
Source dataset
uspto-grants-2015_02
Patent number
US08952162B2

Reaction notes

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