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

HRID 897306노트

반응식

HRID 897306 반응식
[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

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8efa4059e5094718b0bea5ffeab91e0c
출처 데이터셋
uspto-grants-2005_07
특허 번호
US06921759B2

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