Hydrochloric Acid → 5-Amino-2-(6-morpholin-4-ylpyridin-3-yl)-1,3-thiazole-4-carboxylic acid

HRID 2060636Notes

Reaction equation

HRID 2060636 reaction equation
[NH2:1][C:2]1[S:6][C:5]([C:7]2[CH:8]=[N:9][C:10]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[CH:11][CH:12]=2)=[N:4][C:3]=1[C:19]([O:21]CC)=[O:20].CO.[OH-].[K+].Cl>CC(O)(C)C>[NH2:1][C:2]1[S:6][C:5]([C:7]2[CH:8]=[N:9][C:10]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[CH:11][CH:12]=2)=[N:4][C:3]=1[C:19]([OH:21])=[O:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14797Potassium HydroxideHCID 58335250Ethyl 5-amino-2-(6-morpholin-4-ylpyridin-3-yl)-1,3-thiazole-4-carboxylate

Product 1

HCID 583352705-Amino-2-(6-morpholin-4-ylpyridin-3-yl)-1,3-thiazole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
60 °C

Procedure

Ethyl 5-amino-2-(6-morpholin-4-ylpyridin-3-yl)-1,3-thiazole-4-carboxylate (Example 21, Step 4) (100 mg, 0.3 mmol) was taken up in t-BuOH (3 ml) and methanol (3 ml) and 1M aqueous potassium hydroxide (1.5 ml, 1.5 mmol) was added. The resulting mixture was stirred at 60° C. for 4.5 hrs. The reaction was then cooled to room temperature and neutralized with 1.5 mL 1M aqueous HCl. A yellow precipitate then formed. The resulting slurry was concentrated under reduced pressure, re-suspended in MeOH and concentrated again to give the title compound as a yellow solid which was used in the next step without further purification. LRMS (APCI) calc'd for (C13H15N4O3S) [M+H]+, 307.1; found 307.0.

Workup

  1. customA yellow precipitate then formed
  2. concentrationThe resulting slurry was concentrated under reduced pressure
  3. concentrationconcentrated again

Sources & evidence

ORD record
ord-2c88a306adc74ff3b1d2b891529c92e6
Source dataset
uspto-grants-2012_10
Patent number
US08278335B2

Reaction notes

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