Hydrochloric Acid → 4-(2-amino-4-methoxy-benzothiazol-7-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

HRID 1582114Notes

Reaction equation

HRID 1582114 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[C:22]3[S:21][C:20]([NH:23]C(OC)=O)=[N:19][C:18]=3[C:17]([O:28][CH3:29])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl>O1CCOCC1.C(O)CO.[OH-].[Na+]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]=[C:11]([C:14]2[C:22]3[S:21][C:20]([NH2:23])=[N:19][C:18]=3[C:17]([O:28][CH3:29])=[CH:16][CH:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 86588830HCID 86588830, compound

Product 1

HCID 207255094-(2-amino-4-methoxy-benzothiazol-7-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl esterYield 89.9%

Reagents, catalysts & solvents 3

HCID 174Ethylene GlycolSolventHCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

0.9 g (0.002 Mol) 4-(4-methoxy-2-methoxycarbonylamino-benzothiazol-7-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester were dissolved in a mixture of 7 ml dioxane, 14 ml ethylene glycol and 14 ml 2 N NaOH and heated to 100° C. for 15 h. After cooling to room temperature the pH was adjusted to 7 with 1 N HCl. A precipitation formed, which was filtered, washed with water and dried in vacuo to yield 0.65 g (84%) 4-(2-amino-4-methoxy-benzothiazol-7-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester as a light yellow solid; F.p.: 191-196° C.

Workup

  1. temperatureAfter cooling to room temperature the pH
  2. customA precipitation
  3. customformed
  4. filtrationwhich was filtered
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-fe8eff2302104be89af3f322330b02e3
Source dataset
uspto-grants-2004_05
Patent number
US06734179B2

Reaction notes

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