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

HRID 2364337
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HRID 2364337 반응식
[NH2:1][CH2:2][CH2:3][N:4]1[C:13]2[C:8](=[N:9][CH:10]=[C:11]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[CH:12]=2)[C:7]([OH:22])=[C:6]([C:23]([NH:25][CH2:26][CH2:27][OH:28])=[O:24])[C:5]1=[O:29].C(N(C(C)C)CC)(C)C.[C:39](OC(=O)C)(=[O:41])[CH3:40].O>CN(C=O)C>[C:39]([NH:1][CH2:2][CH2:3][N:4]1[C:13]2[C:8](=[N:9][CH:10]=[C:11]([CH2:14][C:15]3[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=3)[CH:12]=2)[C:7]([OH:22])=[C:6]([C:23]([NH:25][CH2:26][CH2:27][OH:28])=[O:24])[C:5]1=[O:29])(=[O:41])[CH3:40]
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HCID 962WaterHCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 694804131-(2-Aminoethyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxyethyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

생성물 1

HCID 694801751-[2-(Acetylamino)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxyethyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
0 °C

실험 절차

A solution of 1-(2-aminoethyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxyethyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (0.019 g, 0.047 mmol) and diisopropyl ethylamine (0.075 mL, 0.43 mmol) in DMF (1 mL) under nitrogen was treated with acetic anhydride (0.004 mL, 0.042 mmol) at ambient temperature. The reaction was warmed slightly to solubilize then reacted at ambient temperature for 10 min. Water was added (2 mL) and the reaction was cooled to 0° C. and concentrated in vacuo. The resulting residue was treated with 1 N NaHSO4 and filtered then triturated with Et2O and dried in air to provide the title compound as an off-white solid: 1H NMR (300 MHz, DMSO-D6) δ ppm 1.7 (s, 3 H), 3.3 (dd, J=3.1, 1.3 Hz, 2 H), 3.4 (m, 2 H), 3.6 (m, 2 H), 4.1 (s, 2 H), 4.3 (m, 2 H), 4.9 (t, J=4.8 Hz, 1 H), 7.1 (t, J=8.8 Hz, 2 H), 7.4 (m, 2 H), 8.0 (m, 1 H), 8.2 (s, 1 H), 8.5 (s, 1 H), 10.4 (d, J=6.2 Hz, 1 H), 17.2 (s, 1 H); ES+ MS: 443 (M+H+).

후처리

  1. temperatureThe reaction was warmed slightly
  2. customto solubilize then reacted at ambient temperature for 10 min
  3. concentrationconcentrated in vacuo
  4. additionThe resulting residue was treated with 1 N NaHSO4
  5. filtrationfiltered
  6. customthen triturated with Et2O
  7. customdried in air

출처 및 근거

ORD 기록
ord-db9c537fa59b4be0b497b7198e22362a
출처 데이터셋
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08691991B2

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