Methanesulfonyl chloride → HCID 67215640, compound

HRID 472920Notes

Reaction equation

HRID 472920 reaction equation
[S:1](Cl)([CH3:4])(=[O:3])=[O:2].Cl.[NH2:7][C:8]1[N:9]=[C:10]([C:17]([C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[C:21]([O:28][CH3:29])[CH:20]=2)=[O:18])[N:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=12>N1C=CC=CC=1.C(OC(C)C)(C)C>[CH3:29][O:28][C:21]1[CH:20]=[C:19]([CH:24]=[CH:23][C:22]=1[N+:25]([O-:27])=[O:26])[C:17]([C:10]1[N:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]2=[C:8]([NH:7][S:1]([CH3:4])(=[O:3])=[O:2])[N:9]=1)=[O:18]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 67215849HCID 67215849, compound

Product 1

HCID 67215640HCID 67215640, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 7914Diisopropyl EtherSolvent

Procedure

116 μl (1.49 mmol) of mesyl chloride are added, under a nitrogen atmosphere at a temperature of 5° C., to 0.473 g (1.36 mmol) of (1-aminoimidazo[1,5-a]pyridin-3-yl)(3-methoxy-4-nitrophenyl)methanone hydrochloride obtained in example 76 in 14 ml of pyridine. On completion of the introduction, the mixture is allowed to return to ambient temperature and is stirred for 30 minutes. The reaction medium is poured under 95 ml of 2N hydrochloric acid and extracted with ethyl acetate. The organic phase is washed with water, separated by settling, dried over sodium sulfate and concentrated under reduced pressure. The solid residue obtained is taken up in isopropyl ether, filtered off, washed with isopropyl ether and then dried. 0.40 g of an orange solid is collected. Melting point: 231° C.; 1H NMR (d6-DMSO): 3.24 (3H, s), 4.02 (3H, s), 7.40-7.44 (1H, m), 7.49-7.53 (1H, m), 7.88-7.92 (1H, d), 8.00-8.07 (2H, m), 8.26 (1H, s), 9.75 (1H, d)

Workup

  1. customto return to ambient temperature
  2. additionThe reaction medium is poured under 95 ml of 2N hydrochloric acid
  3. extractionextracted with ethyl acetate
  4. washThe organic phase is washed with water
  5. customseparated
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe solid residue obtained
  9. filtrationfiltered off
  10. washwashed with isopropyl ether
  11. customdried
  12. custom0.40 g of an orange solid is collected

Sources & evidence

ORD record
ord-9105869ff2a64456a815615c9786069e
Source dataset
uspto-grants-2014_01
Patent number
US08633216B2

Reaction notes

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