Hydrochloric Acid → HCID 10474424, compound

HRID 2376638Notes

Reaction equation

HRID 2376638 reaction equation
C([O:3][C:4](=[O:30])[CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:13]=[C:14]3[C:19](=[C:20]([C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([C:28]#[N:29])[CH:23]=4)[N:21]=2)[N:18]=[CH:17][CH:16]=[CH:15]3)[CH2:8][CH2:7]1)C.[OH-].[K+].Cl>C(O)C>[C:28]([C:24]1[CH:23]=[C:22]([C:20]2[N:21]=[C:12]([N:9]3[CH2:8][CH2:7][CH:6]([CH2:5][C:4]([OH:30])=[O:3])[CH2:11][CH2:10]3)[CH:13]=[C:14]3[C:19]=2[N:18]=[CH:17][CH:16]=[CH:15]3)[CH:27]=[CH:26][CH:25]=1)#[N:29]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 69207093HCID 69207093, compound

Product 1

HCID 10474424HCID 10474424, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
45 °C

Procedure

{1-[8-(3-Cyano-phenyl)-[1,7]naphthyridin-6-yl]-piperidin-4-yl}-acetic acid ethyl ester (250 mg, 0.62 mmol) is dissolved in ethanol (5 ml) with 2M KOH (aq., 0.95 ml, 1.86 mmol) and the mixture stirred at 45° C. for 0.5 hours. After cooling, the pH of the mixture is adjusted to pH 3 by the dropwise addition of concentrated HCl. After stirring for 0.5 hours, the resultant solid is filtered and washed with water to yield the desired product. M.p. 178-180° C.

Workup

  1. temperatureAfter cooling
  2. stirringAfter stirring for 0.5 hours
  3. filtrationthe resultant solid is filtered
  4. washwashed with water

Sources & evidence

ORD record
ord-7bbf4274573e480981494e56c4acbf8f
Source dataset
uspto-grants-2008_12
Patent number
US07468370B2

Reaction notes

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