HCID 86711369, compound → HCID 86711371, compound

HRID 926297Notes

Reaction equation

HRID 926297 reaction equation
C(OC([NH:8][CH2:9][C:10]([N:12]1[CH:21]([CH2:22][C:23]([O-:25])=[O:24])[C:20]2[N:19]=[CH:18][CH:17]=[C:16]([Cl:26])[C:15]=2[CH2:14][CH2:13]1)=[O:11])=O)(C)(C)C.[Na+]>O1CCOCC1.Cl>[Cl-:26].[C:23]([CH2:22][CH:21]1[C:20]2[N:19]=[CH:18][CH:17]=[C:16]([Cl:26])[C:15]=2[CH2:14][CH2:13][N:12]1[C:10](=[O:11])[CH2:9][NH3+:8])([OH:25])=[O:24]

Participants

4

Reactant 1

HCID 86711369HCID 86711369, compound

Product 1

HCID 86711371HCID 86711371, compoundYield 261.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent2×

Procedure

94-8. To a stirred suspension of sodium 2-(7-(2-((tert-butoxycarbonyl)amino)acetyl)-4-chloro-5,6,7,8-tetrahydro-1,7-naphthyridin-8-yl)acetate (540 mg, 1.41 mmol) in dioxane (10 mL), 4N HCl in dioxane (1.76 mL, 7.03 mmol) was added and the reaction mixture was stirred at RT for 48 h. The beige precipitate was filtered off washed with a small amount of diethyl ether (2×). The HCl salt was dried under high vacuo overnight to yield the title compound as beige solid (590 mg) containing a residual amount of NaCl. UPLC-MS: MS 284.1 (M+H+); UPLC rt 0.45 min.

Workup

  1. additionwas added
  2. filtrationThe beige precipitate was filtered off
  3. washwashed with a small amount of diethyl ether (2×)
  4. dry with materialThe HCl salt was dried under high vacuo overnight

Sources & evidence

ORD record
ord-e9386dec34154f6091d21ec057052396
Source dataset
uspto-grants-2016_03
Patent number
US09284331B2

Reaction notes

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