HCID 86588844, compound → 2-methoxy-N-(4-methoxy-7-piperidin-4-yl-benzothiazol-2-yl)-isonicotinamide

HRID 1582137Notes

Reaction equation

HRID 1582137 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]([O:32][CH3:33])[CH:27]=4)=[O:25])=[N:19][C:18]=3[C:17]([O:34][CH3:35])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C>Cl.CO>[CH3:33][O:32][C:28]1[CH:27]=[C:26]([CH:31]=[CH:30][N:29]=1)[C:24]([NH:23][C:20]1[S:21][C:22]2[C:14]([CH:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)=[CH:15][CH:16]=[C:17]([O:34][CH3:35])[C:18]=2[N:19]=1)=[O:25]

Participants

3

Reactant 1

HCID 86588844HCID 86588844, compound

Product 1

HCID 227195582-methoxy-N-(4-methoxy-7-piperidin-4-yl-benzothiazol-2-yl)-isonicotinamideYield 94.1%

Reagents, catalysts & solvents 1

HCID 21893726Hydrochloride methanolSolvent

Procedure

0.10 g (0.20 mMol) 4-{4-methoxy-2-[(2-methoxy-pyridine-4-carbonyl)-amino]-benzothiazol-7-yl}-piperidine-1-carboxylic acid tert-butyl ester were dissolved in 2 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 3 ml isopropanol. The suspension formed was filtered and the material on the filter was washed with diethyl ether and dried in vacuo. One obtained 0.075 g (86%) 2-methoxy-N-(4-methoxy-7-piperidin-4-yl-benzothiazol-2-yl)-isonicotinamide 1:2 hydrochloride as a yellow solid. F.p.: 305-310° 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-6629298cf22748d59877a604426b4c71
Source dataset
uspto-grants-2004_05
Patent number
US06734179B2

Reaction notes

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