Chloride → 1-(2-{[(Dimethylamino)carbonyl]amino}ethyl)-N-[2-(ethyloxy)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

HRID 2364351ノート

反応式

HRID 2364351 の反応式
[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][O:28][CH2:29][CH3:30])=[O:24])[C:5]1=[O:31].C(N(C(C)C)CC)(C)C.[Cl-].[CH3:42][N:43]([CH:45]=[O:46])[CH3:44]>>[CH3:42][N:43]([CH3:44])[C:45]([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][O:28][CH2:29][CH3:30])=[O:24])[C:5]1=[O:31])=[O:46]

参加物

5

反応物 4

HCID 312ChlorideHCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 694808831-(2-Aminoethyl)-N-[2-(ethyloxy)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

生成物 1

HCID 694801991-(2-{[(Dimethylamino)carbonyl]amino}ethyl)-N-[2-(ethyloxy)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

実験手順

A solution of 1-(2-aminoethyl)-N-[2-(ethyloxy)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (0.02 g, 0.047 mmol) and diisopropyl ethylamine (0.041 mL, 0.24 mmol) in DMF (5 mL) under nitrogen was treated with N,N-dimethyl carbonyl chloride (0.0043 mL, 0.047 mmol) at ambient temperature. After 2 h, an additional 0.001 mL of the chloride was added and the was stirred at ambient temperature for an additional 6 h. The reaction was concentrated in vacuo and the resulting residue suspended in DMSO and water, filtered, then washed with water and Et2O before drying in vacuo to provide the title compound as an off-white solid: 1H NMR (400 MHz, DMSO-D6) δ ppm 1.1 (t, J=7.0 Hz, 3 H), 2.7 (s, 6 H), 3.3 (d, J=7.0 Hz, 2 H), 3.5 (q, J=7.0 Hz, 2 H), 3.5 (s, 4 H), 4.1 (s, 2 H), 4.2 (t, J=6.1 Hz, 2 H), 6.6 (m, 1 H), 7.1 (t, J=8.9 Hz, 2 H), 7.4 (dd, J=8.8, 5.5 Hz, 2 H), 8.3 (s, 1 H), 8.5 (s, 1 H), 10.4 (s, 1 H); ES+ MS: 500 (M+H+).

後処理

  1. concentrationThe reaction was concentrated in vacuo
  2. filtrationwater, filtered
  3. washwashed with water and Et2O
  4. custombefore drying in vacuo

出典と根拠

ORDレコード
ord-61d67f5f3df34247b49134dbec9ee0cb
出典データセット
uspto-grants-2014_04
特許番号
US08691991B2

反応ノート

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