Methyl chloroformate → Methyl {2-[3-({[2-(ethyloxy)ethyl]amino}carbonyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,5-naphthyridine-1(2H)-yl]ethyl}carbamate

HRID 2364347ノート

反応式

HRID 2364347 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[C:42]([O:44][CH3:45])=[O:43]>CN(C=O)C>[CH2:29]([O:28][CH2:27][CH2:26][NH:25][C:23]([C:6]1[C:5](=[O:31])[N:4]([CH2:3][CH2:2][NH:1][C:42](=[O:43])[O:44][CH3:45])[C:13]2[C:8]([C:7]=1[OH:22])=[N:9][CH:10]=[C:11]([CH2:14][C:15]1[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=1)[CH:12]=2)=[O:24])[CH3:30]

参加物

5

反応物 3

HCID 6586Methyl chloroformateHCID 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 86612781Methyl {2-[3-({[2-(ethyloxy)ethyl]amino}carbonyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,5-naphthyridine-1(2H)-yl]ethyl}carbamate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

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 methyl chloroformate (0.0036 mL, 0.047 mmol) at ambient temperature. The reaction was concentrated in vacuo and the resulting residue treated with 1 N NaHSO4, filtered, then washed with 1 N NaHSO4 and Et2O before drying in vacuo to provide the title compound as an off-white solid: 1H NMR (300 MHz, DMSO-D6) δ ppm 1.1 (t, J=7.0 Hz, 3 H), 3.3 (m, 2 H), 3.4 (s, 3 H), 3.5 (m, 7 H), 4.1 (s, 2 H), 4.3 (t, J=6.0 Hz, 2 H), 7.1 (t, J=8.8 Hz, 2 H), 7.3 (m, 1 H), 7.4 (m, 2 H), 8.1 (s, 1 H), 8.5 (s, 1 H), 17.1 (s, 1 H); ES+ MS: 487 (M+H+).

後処理

  1. concentrationThe reaction was concentrated in vacuo
  2. additionthe resulting residue treated with 1 N NaHSO4
  3. filtrationfiltered
  4. washwashed with 1 N NaHSO4 and Et2O
  5. custombefore drying in vacuo

出典と根拠

ORDレコード
ord-3817395a13bf468db01b8f16dbb822b5
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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