Hydrochloride methanol → N-(4-methoxy-7-piperidin-4-yl-benzothiazol-2-yl)-2-methyl-isonicotinamide hydrochloride

HRID 1582127Notes

Reaction equation

HRID 1582127 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:22]3[S:21][C:20]([NH:23][C:24]([C:26]4[CH:31]=[CH:30][N:29]=[C:28]([CH3:32])[CH:27]=4)=[O:25])=[N:19][C:18]=3[C:17]([O:33][CH3:34])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:35].CO>>[ClH:35].[CH3:34][O:33][C:17]1[C:18]2[N:19]=[C:20]([NH:23][C:24](=[O:25])[C:26]3[CH:31]=[CH:30][N:29]=[C:28]([CH3:32])[CH:27]=3)[S:21][C:22]=2[C:14]([CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)=[CH:15][CH:16]=1

Participants

3

Reactant 2

HCID 21893726Hydrochloride methanolHCID 865888394-{4-Methoxy-2-[(2-methyl-pyridine-4-carbonyl)-amino]-benzothiazol-7-yl}-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 22719536N-(4-methoxy-7-piperidin-4-yl-benzothiazol-2-yl)-2-methyl-isonicotinamide hydrochlorideYield 57%

Procedure

0.15 g (0.31 mMol) 4-{4-methoxy-2-[(2-methyl-pyridine-4-carbonyl)-amino]-benzothiazol-7-yl}-piperidine-1-carboxylic acid tert-butyl ester were dissolved in 4 ml 2.5 M HCl/MeOH and heated to reflux for 1.5 h. The reaction mixture was concentrated in vacuo and taken up in 5 ml isopropanol. The suspension formed was filtered and the material on the filter was washed with diethyl ether and dried in vacuo. One obtained 80 mg (57%) N-(4-methoxy-7-piperidin-4-yl-benzothiazol-2-yl)-2-methyl-isonicotinamide hydrochloride (1:2) as a white solid. F.p.: 272-277° C.

Workup

  1. temperatureheated
  2. temperatureto reflux for 1.5 h
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customThe suspension formed
  5. filtrationwas filtered
  6. washthe material on the filter was washed with diethyl ether
  7. customdried in vacuo

Sources & evidence

ORD record
ord-7c7fcad57ca74844a2f2fcd8debd3723
Source dataset
uspto-grants-2004_05
Patent number
US06734179B2

Reaction notes

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