HCID 86588830, compound → [4-Methoxy-7-(1,2,3,6-tetrahydro-pyridin-4-yl)-benzothiazol-2-yl]-carbamic acid methyl ester

HRID 1582113Notes

Reaction equation

HRID 1582113 reaction equation
C(OC([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[C:22]3[S:21][C:20]([NH:23][C:24]([O:26][CH3:27])=[O:25])=[N:19][C:18]=3[C:17]([O:28][CH3:29])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C>Cl.CO>[CH3:27][O:26][C:24](=[O:25])[NH:23][C:20]1[S:21][C:22]2[C:14]([C:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH:10]=3)=[CH:15][CH:16]=[C:17]([O:28][CH3:29])[C:18]=2[N:19]=1

Participants

3

Reactant 1

HCID 86588830HCID 86588830, compound

Product 1

HCID 86588831[4-Methoxy-7-(1,2,3,6-tetrahydro-pyridin-4-yl)-benzothiazol-2-yl]-carbamic acid methyl esterYield 18%

Reagents, catalysts & solvents 1

HCID 21893726Hydrochloride methanolSolvent

Procedure

0.03 g (0.072 mMol) 4-(4-methoxy-2-methoxycarbonylamino-benzothiazol-7-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester were dissolved in 0.75 ml 2.5 M HCl/MeOH and heated to reflux for 1.5 h. The reaction mixture was concentrated in vacuo, taken up in 3 ml water and the pH was adjusted to 8 with sat. aqueous sodium bicarbonate. The suspension formed was filtered and the material on the filter was washed with water and dried in vacuo. The residue was subjected to column chromatography (dichloro methane/methanol 9:1+1%) NH4OH) to yield 4 mg (18%) [4-methoxy-7-(1,2,3,6-tetrahydro-pyridin-4-yl)-benzothiazol-2-yl]-carbamic acid methyl ester as a beige solid. ES-MS m/e (%): 320 ([M+H]+, 100).

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 water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-acf7235a3f104c7391931dfc4f9f36b5
Source dataset
uspto-grants-2004_05
Patent number
US06734179B2

Reaction notes

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