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 1881739노트

반응식

HRID 1881739 반응식
[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]

참가 물질

4

반응물 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

생성물 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 hydrochloride수율 148.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-429e8bbdd0c64985b10055668bf59dba
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08318940B2

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