Methanesulfonyl chloride → HCID 58114930, compound

HRID 241769Notes

Reaction equation

HRID 241769 reaction equation
[Cl:1][C:2]1[C:3]([C:9]2[C:18]([OH:19])=[N:17][C:12]3=[N:13][CH:14]=[CH:15][N:16]=[C:11]3[C:10]=2[OH:20])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.C(N(C(C)C)C(C)C)C.[CH3:30][S:31](Cl)(=[O:33])=[O:32]>ClCCl.Cl>[Cl:1][C:2]1[C:3]([C:9]2[C:18](=[O:19])[NH:17][C:12]3=[N:13][CH:14]=[CH:15][N:16]=[C:11]3[C:10]=2[O:20][S:31]([CH3:30])(=[O:33])=[O:32])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

6

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 178517382HCID 178517382, compound

Product 1

HCID 58114930HCID 58114930, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 7-(3,5-dichloro-pyrid-2-yl)-pyrido[2,3-b]pyrazine-6,8-diol (Example 1.2) (0.20 g) and N-ethyl-diisopropylamine (0.126 g) in dry dichloromethane (15 ml) was added methane sulfonyl chloride (0.074 g). The reaction mixture was stirred at ambient temperature for one hour and then stored at ambient temperature for 16 hours. The reaction mixture was diluted with aqueous hydrochloric acid (1M). The phases were separated and the organic layer was concentrated. The residue was purified by reverse phase HPLC to give Compound No. A4 of Table A as a pale brown solid (0.055 g).

Workup

  1. waitstored at ambient temperature for 16 hours
  2. customThe phases were separated
  3. concentrationthe organic layer was concentrated
  4. customThe residue was purified by reverse phase HPLC
  5. customto give Compound No

Sources & evidence

ORD record
ord-488170bbe07f4dff8640dc87d60cb842
Source dataset
uspto-grants-2014_02
Patent number
US08653078B2

Reaction notes

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