Ethanolamine → 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxyethyl)-1-(3-hydroxypropyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

HRID 2364372노트

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[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13]([OH:29])=[C:14]([C:24](OCC)=[O:25])[C:15](=[O:23])[N:16]3[CH2:19][CH2:20][CH2:21][OH:22])=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[NH2:30][CH2:31][CH2:32][OH:33]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13]([OH:29])=[C:14]([C:24]([NH:30][CH2:31][CH2:32][OH:33])=[O:25])[C:15](=[O:23])[N:16]3[CH2:19][CH2:20][CH2:21][OH:22])=[N:11][CH:10]=2)=[CH:4][CH:3]=1

참가 물질

반응물 2

HCID 700Ethanolamine

HCID 69481032HCID 69481032, 화합물

생성물 1

HCID 694821267-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxyethyl)-1-(3-hydroxypropyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide수율 46%

실험 절차

In a similar manner to that described in example 196, from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-(3-hydroxypropyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (27 mg, 0.0675 mmol) and 2-aminoethanol (0.05 mL) was prepared 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxyethyl)-1-(3-hydroxypropyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (13 mg, 46% yield) as a white solid after purification by reverse phase HPLC. 1H NMR (CDCl3) δ 10.28 (br s, 1 H), 8.52 (s, 1 H), 7.51 (1 H), 7.15-7.11 (m, 2 H), 7.01-6.96 (m, 2 H), 4.27 (m, 2 H), 4.10 (s, 2 H), 3.76 (m, 2 H), 3.57 (m, 2 H), 3.49 (m, 2 H), 1.79 (m, 2 H); HRMS m/z calcd for C21H23N3O5F: 416.1622. Found: 416.1634.

출처 및 근거

ORD 기록: ord-0f681c48ff4f432fb3ba333718ca90bd
출처 데이터셋: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US08691991B2

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