Hydrochloric Acid → HCID 86665050, compound

HRID 1047168Notes

Reaction equation

HRID 1047168 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][N:11]=1)[N:8]([C@H:12]1[CH2:17][CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13]1)[CH:7]=[C:6]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:5]2=[O:30].[ClH:31]>ClCCl>[ClH:31].[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][N:11]=1)[N:8]([C@H:12]1[CH2:17][CH2:16][CH2:15][NH:14][CH2:13]1)[CH:7]=[C:6]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:5]2=[O:30]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86665052HCID 86665052, compound2×

Product 1

HCID 86665050HCID 86665050, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-ethyl 6-bromo-1-(1-(tert-butoxycarbonyl)piperidin-3-yl)-4-oxo-1,4-dihydro-1,7-naphthyridine-3-carboxylate (Intermediate 54, 6.37 g, 13.26 mmol, 1 equiv.) in dichloromethane (53 mL) was added 4 N hydrogen chloride (13.26 mL, 53.04 mmol, 4 equiv.). This was stirred at room temperature for 8 h. The precipitate was washed with diethyl ether and dried to provide (S)-ethyl 6-bromo-4-oxo-1-(piperidin-3-yl)-1,4-dihydro-1,7-naphthyridine-3-carboxylate hydrochloride as a solid (4.67 g, >99%).

Workup

  1. washThe precipitate was washed with diethyl ether
  2. customdried

Sources & evidence

ORD record
ord-cf718151dac3473e97937d371467ebca
Source dataset
uspto-grants-2013_10
Patent number
US08569484B2

Reaction notes

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