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

HRID 1881735Notes

Reaction equation

HRID 1881735 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]([F:30])[CH:28]=4)[CH:23]=[CH:22][C:21]3=[O:31])[CH2:14][C@H:13]2[OH:32])[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]([F:30])[CH:28]=4)[CH:23]=[CH:22][C:21]3=[O:31])[CH2:14][C@H:13]2[OH:32])[CH:5]=[N:6][C:7]=1[CH2:8][OH:9]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 468463881-{2-[(3R,4S)-4-({[5-chloro-6-(hydroxymethyl)-3-pyridinyl]methyl}amino)-3-hydroxy-1-piperidinyl]ethyl}-7-fluoro-1,5-naphthyridin-2(1H)-one

Product 1

HCID 468463891-{2-[(3R,4S)-4-({[5-chloro-6-(hydroxymethyl)-3-pyridinyl]methyl}amino)-3-hydroxy-1-piperidinyl]ethyl}-7-fluoro-1,5-naphthyridin-2(1H)-one hydrochlorideYield 185.7%

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-fluoro-1,5-naphthyridin-2(1H)-one (Example 3: 19.5 mg, 0.042 mmol) in DCM (2 ml) at 0° C. was added HCl (4M in 1,4-dioxane) (10.64 μl, 0.043 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-fluoro-1,5-naphthyridin-2(1H)-one hydrochloride (19.5 mg, 0.039 mmol, 92% 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-79df3d67a12f4f52a36f384077577b1c
Source dataset
uspto-grants-2012_11
Patent number
US08318940B2

Reaction notes

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