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

HRID 1698074Notes

Reaction equation

HRID 1698074 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].N1C=CC=CC=1.[CH3:11][O:12][C:13]1[N:18]=[CH:17][C:16]([C:19]2[S:20][C:21]3[CH:27]=[C:26]([NH2:28])[CH:25]=[CH:24][C:22]=3[N:23]=2)=[CH:15][CH:14]=1>C(Cl)Cl>[CH3:11][O:12][C:13]1[N:18]=[CH:17][C:16]([C:19]2[S:20][C:21]3[CH:27]=[C:26]([NH:28][C:1](=[O:3])[CH3:2])[CH:25]=[CH:24][C:22]=3[N:23]=2)=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 248035652-(6-Methoxypyridin-3-yl)-1,3-benzothiazol-6-amine

Product 1

HCID 24803566N-[2-(6-methoxypyridin-3-yl)-1,3-benzothiazol-6-yl]acetamideYield 39.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetylchloride (3 μL, 0.037 mmol) and pyridine (3 μL, 0.037 mmol) was added to a sol. of 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. o.n. Half of the solvent was distilled of in vacuo and a few drops of hexane were added. The precipitated solid was collected and dried in vacuo, to give the title compound (4 mg) as a white solid. 1H NMR δ 10.30 (s, 1H) 8.91 (d, 1H) 8.57 (d, 1H) 8.39 (dd, 1H) 8.03 (d, 1H) 7.63 (dd, 1H) 7.08 (d, 1H) 4.02 (s, 3H) 2.16 (s, 3H); MS m/z (M+H) 300, (M−H) 298.

Workup

  1. distillationHalf of the solvent was distilled of in vacuo and a few drops of hexane
  2. additionwere added
  3. customThe precipitated solid was collected
  4. customdried in vacuo

Sources & evidence

ORD record
ord-ca3c6e4a3a174b6bab0eb81a55c49695
Source dataset
uspto-grants-2012_04
Patent number
US08163928B2

Reaction notes

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