Pyridine → N-[2-(6-methoxypyridin-3-yl)-1,3-benzothiazol-6-yl]methanesulfonamide

HRID 1698075Notes

Reaction equation

HRID 1698075 reaction equation
[S:1](Cl)([CH3:4])(=[O:3])=[O:2].N1C=CC=CC=1.[CH3:12][O:13][C:14]1[N:19]=[CH:18][C:17]([C:20]2[S:21][C:22]3[CH:28]=[C:27]([NH2:29])[CH:26]=[CH:25][C:23]=3[N:24]=2)=[CH:16][CH:15]=1>C(Cl)Cl.CCCCCC>[CH3:12][O:13][C:14]1[N:19]=[CH:18][C:17]([C:20]2[S:21][C:22]3[CH:28]=[C:27]([NH:29][S:1]([CH3:4])(=[O:3])=[O:2])[CH:26]=[CH:25][C:23]=3[N:24]=2)=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 248035652-(6-Methoxypyridin-3-yl)-1,3-benzothiazol-6-amine

Product 1

HCID 24803567N-[2-(6-methoxypyridin-3-yl)-1,3-benzothiazol-6-yl]methanesulfonamideYield 70.2%

Reagents, catalysts & solvents 2

HCID 8058HexaneCatalystHCID 6344DichloromethaneSolvent

Procedure

Mesylchloride (3 μL, 0.037 mmol) and pyridine (3 μL, 0.037 mmol) was added to a sol. 2-(6-methoxypyridin-3-yl)-1,3-benzothiazol-6-amine (9 mg, 0.034 mmol) in DCM (1 mL). The r.m. was stirred at r.t. for 6 days. A few drops of hexane was added and the precipitated solid was collected and dried in vacuo. The crude product was purified by flash column chromatography (20 to 100% ethyl acetate in heptane), to give the title compound (8 mg) as an off-white solid. 1H NMR δ 9.84 (s, 1H) 8.63 (d, 1H) 8.11 (dd, 1H) 7.77 (d, 1H) 7.71 (d, 1H) 7.14 (dd, 1H) 6.79 (d, 1H) 3.73 (s, 3H) 2.82 (s, 3H); MS m/z (M+H) 336, (M−H) 334.

Workup

  1. customthe precipitated solid was collected
  2. customdried in vacuo
  3. customThe crude product was purified by flash column chromatography (20 to 100% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-152e44b34c4d4c438e5fd20b7bec71d2
Source dataset
uspto-grants-2012_04
Patent number
US08163928B2

Reaction notes

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