Pyridine → HCID 57675191, compound

HRID 490920Notes

Reaction equation

HRID 490920 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].Cl.[CH2:7]([N:9]1[C:13]2[N:14]=[CH:15][C:16]([C:25]3[O:29][N:28]=[C:27]([CH2:30][CH:31]4[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]4)[N:26]=3)=[C:17]([NH:18][CH:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)[C:12]=2[CH:11]=[N:10]1)[CH3:8].N1C=CC=CC=1>C(Cl)(Cl)Cl>[CH2:7]([N:9]1[C:13]2[N:14]=[CH:15][C:16]([C:25]3[O:29][N:28]=[C:27]([CH2:30][CH:31]4[CH2:36][CH2:35][N:34]([S:2]([CH3:1])(=[O:4])=[O:3])[CH2:33][CH2:32]4)[N:26]=3)=[C:17]([NH:18][CH:19]3[CH2:20][CH2:21][O:22][CH2:23][CH2:24]3)[C:12]=2[CH:11]=[N:10]1)[CH3:8]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 67529443HCID 67529443, compound

Product 1

HCID 57675191HCID 57675191, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Methanesulphonyl chloride (1.16 mmol) was added to a stirred solution of Intermediate 125 (0.033 mmol) and pyridine (0.5 ml) in chloroform (1 ml) at room temperature. After stirring at room temperature for 31 h, the reaction mixture was applied to a SPE cartridge (aminopropyl, 5 g) and the cartridge was eluted sequentially with chloroform, ethyl acetate and methanol. Fractions containing the desired product were evaporated in vacuo. The resulting residue was further purified on a SPE cartridge (silica, 1 g) eluting with a gradient of 30-100% ethyl acetate in petroleum ether to afford Example 176. LCMS showed MH+=490, TRET=2.97 min.

Workup

  1. washthe cartridge was eluted sequentially with chloroform, ethyl acetate and methanol
  2. additionFractions containing the desired product
  3. customwere evaporated in vacuo
  4. customThe resulting residue was further purified on a SPE cartridge (silica, 1 g)
  5. washeluting with a gradient of 30-100% ethyl acetate in petroleum ether
  6. customto afford Example 176
  7. customMH+=490, TRET=2.97 min.

Sources & evidence

ORD record
ord-25299d7b274e4f40b3f12ea1336439f2
Source dataset
uspto-grants-2009_05
Patent number
US07528148B2

Reaction notes

Loading…