Methanesulfonyl chloride → HCID 11267733, compound

HRID 2054359Notes

Reaction equation

HRID 2054359 reaction equation
[S:1]([NH:11][C:12]1[N:17]2[C:18]3[N:24]=[CH:23][CH:22]=[CH:21][C:19]=3[CH:20]=[C:16]2[C:15](O)=[CH:14][N:13]=1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].CS(Cl)(=O)=O>C(Cl)Cl>[S:1]([NH:11][C:12]1[N:17]2[C:18]3[N:24]=[CH:23][CH:22]=[CH:21][C:19]=3[CH:20]=[C:16]2[CH:15]=[CH:14][N:13]=1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:2])=[O:3]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 68883999HCID 68883999, compound

Product 1

HCID 11267733HCID 11267733, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 9-tosylamino-6-hydroxypyrido[3′,2′:4,5]pyrrolo[1,2-c]pyrimidine (170 mg, 0.48 mmol) and TEA (133 μl, 0.96 mmol) was dissolved in CH2Cl2 (25 ml), methanesulfonylchloride (37 μl, 0.48 mmol) was dropwise added and the mixture was stirred for 20 min. The solution was washed with water and the organic solutions was dried and evaporated. The crude mixture was purified by flash column chromatography. Elution with CH2Cl2/MeOH (98/2) gave 23a (124 mg, 78%) as a yellow solid.

Workup

  1. washThe solution was washed with water
  2. customthe organic solutions was dried
  3. customevaporated
  4. customThe crude mixture was purified by flash column chromatography
  5. washElution with CH2Cl2/MeOH (98/2)

Sources & evidence

ORD record
ord-62e44812ddfc4531b4921a7fe2b5a8c2
Source dataset
uspto-grants-2008_02
Patent number
US07329666B2

Reaction notes

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