Hydrochloric Acid → N-(4-Fluorobenzyl)-5-{[2-(dimethylamino)-2-oxoethyl]sulfanyl}-8-hydroxy-[1,6]napthyridine-7-carboxamide

HRID 897306Notes

Reaction equation

HRID 897306 reaction equation
[F:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19]([OH:20])=[C:18]3[C:13]([CH:14]=[CH:15][CH:16]=[N:17]3)=[C:12]([S:21][CH2:22][C:23]([OH:25])=O)[N:11]=2)=[O:9])=[CH:4][CH:3]=1.Cl.[CH3:29][NH:30][CH3:31].ON1C2N=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(C(C)C)CC)(C)C.Cl>CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19]([OH:20])=[C:18]3[C:13]([CH:14]=[CH:15][CH:16]=[N:17]3)=[C:12]([S:21][CH2:22][C:23]([N:30]([CH3:31])[CH3:29])=[O:25])[N:11]=2)=[O:9])=[CH:26][CH:27]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 10473Dimethylamine, hydrochlorideHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22346250[(7-{[(4-Fluorobenzyl)amino]carbonyl}-8-hydroxy[1,6]naphthyridin-5-yl)sulfanyl]acetic Acid

Product 1

HCID 22346301N-(4-Fluorobenzyl)-5-{[2-(dimethylamino)-2-oxoethyl]sulfanyl}-8-hydroxy-[1,6]napthyridine-7-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of the carboxylic acid from Step 1 (0.18 g, 0.46 mmol), dimethylamine hydrochloride (56 mg, 0.69 mmol), 1-hydroxy-7-azabenzotriazole (62 mg, 0.46 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (106 mg, 0.55 mmol), and diisopropylethylamine (0.2 mL, 0.46 mmol) in DMF (2.3 mL) was stirred at room temperature overnight. The product mixture was treated with 1 M aq HCl at 0° C. The resulting yellow solid was filtered, washed with diethyl ether. The solid was dissolved in DMSO and subjected to HPLC purification on C-18 stationary phase eluted with water/acetonitrile/TFA mobile phase. Collection and lyophilization of appropriate fractions provide the title compound as yellow solid.

Workup

  1. filtrationThe resulting yellow solid was filtered
  2. washwashed with diethyl ether
  3. dissolutionThe solid was dissolved in DMSO
  4. customsubjected to HPLC purification on C-18 stationary phase
  5. washeluted with water/acetonitrile/TFA mobile phase
  6. customCollection and lyophilization of appropriate fractions

Sources & evidence

ORD record
ord-8efa4059e5094718b0bea5ffeab91e0c
Source dataset
uspto-grants-2005_07
Patent number
US06921759B2

Reaction notes

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