Hydrochloric Acid → 1-{2-[(3R,4S)-4-({[5-chloro-6-(hydroxymethyl)-3-pyridinyl]methyl}amino)-3-hydroxy-1-piperidinyl]ethyl}-7-(methyloxy)-1,5-naphthyridin-2(1H)-one hydrochloride

HRID 1881739Notes

Reaction equation

HRID 1881739 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:10][NH:11][C@H:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][N:20]3[C:29]4[C:24](=[N:25][CH:26]=[C:27]([O:30][CH3:31])[CH:28]=4)[CH:23]=[CH:22][C:21]3=[O:32])[CH2:14][C@H:13]2[OH:33])[CH:5]=[N:6][C:7]=1[CH2:8][OH:9].Cl>C(Cl)Cl>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH2:10][NH:11][C@H:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][N:20]3[C:29]4[C:24](=[N:25][CH:26]=[C:27]([O:30][CH3:31])[CH:28]=4)[CH:23]=[CH:22][C:21]3=[O:32])[CH2:14][C@H:13]2[OH:33])[CH:5]=[N:6][C:7]=1[CH2:8][OH:9]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 468464921-{2-[(3R,4S)-4-({[5-chloro-6-(hydroxymethyl)-3-pyridinyl]methyl}amino)-3-hydroxy-1-piperidinyl]ethyl}-7-(methyloxy)-1,5-naphthyridin-2(1H)-one

Product 1

HCID 468464931-{2-[(3R,4S)-4-({[5-chloro-6-(hydroxymethyl)-3-pyridinyl]methyl}amino)-3-hydroxy-1-piperidinyl]ethyl}-7-(methyloxy)-1,5-naphthyridin-2(1H)-one hydrochlorideYield 148.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-{2-[(3R,4S)-4-({[5-chloro-6-(hydroxymethyl)-3-pyridinyl]methyl}amino)-3-hydroxy-1-piperidinyl]ethyl}-7-(methyloxy)-1,5-naphthyridin-2(1H)-one (Example 7 above: 179.8 mg, 0.379 mmol) in DCM (2.5 ml) at 0° C. was added HCl (1M in diethyl ether) (0.417 ml, 0.417 mmol). The reaction mixture was stirred at rt for 30 min, the solvent was evaporated under vacuum and the crude was dispersed in hexane/DCM. The precipitated solid was isolated by filtration under vacuum and washed with DCM and hexane. The obtained solid was dried overnight at 40° C. under vacuum to give 1-{2-[(3R,4S)-4-({[5-chloro-6-(hydroxymethyl)-3-pyridinyl]methyl}amino)-3-hydroxy-1-piperidinyl]ethyl}-7-(methyloxy)-1,5-naphthyridin-2(1H)-one hydrochloride (143.7 mg, 0.282 mmol, 74.2% yield) as a white solid.

Workup

  1. customthe solvent was evaporated under vacuum
  2. additionthe crude was dispersed in hexane/DCM
  3. customThe precipitated solid was isolated by filtration under vacuum
  4. washwashed with DCM and hexane
  5. customThe obtained solid was dried overnight at 40° C. under vacuum

Sources & evidence

ORD record
ord-429e8bbdd0c64985b10055668bf59dba
Source dataset
uspto-grants-2012_11
Patent number
US08318940B2

Reaction notes

Loading…