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

HRID 2364386
ノート
印刷プレビュー

反応式

HRID 2364386 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][CH:29]([CH3:31])[CH3:30])=[O:24])[C:5]1=[O:32].C(N(C(C)C)CC)(C)C.Cl[C:43]([O:45][CH3:46])=[O:44]>CN(C=O)C>[F:21][C:18]1[CH:17]=[CH:16][C:15]([CH2:14][C:11]2[CH:12]=[C:13]3[C:8]([C:7]([OH:22])=[C:6]([C:23]([NH:25][CH2:26][CH2:27][O:28][CH:29]([CH3:30])[CH3:31])=[O:24])[C:5](=[O:32])[N:4]3[CH2:3][CH2:2][NH:1][C:43](=[O:44])[O:45][CH3:46])=[N:9][CH:10]=2)=[CH:20][CH:19]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 694825271-(2-Aminoethyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-{2-[(1-methylethyl)oxy]ethyl}-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

生成物 1

HCID 86612783Methyl {2-[7-[(4-fluorophenyl)methyl]-4-hydroxy-3-[({2-[(1-methylethyl)oxy]ethyl}amino)carbonyl]-2-oxo-1,5-naphthyridine-1(2H)-yl]ethyl}carbamate

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

実験手順

A solution of 1-(2-aminoethyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-{2-[(1-methylethyl)oxy]ethyl}-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (0.020 g, 0.045 mmol) and diisopropyl ethylamine (0.04 mL, 0.23 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 was treated with 1N NaHSO4. The resulting suspension was filtered, washed with EtOH and Et2O, and dried in vacuo to provide the title compound as an beige solid: 1H NMR (300 MHz, DMSO-d6) δ ppm 1.12 (d, J=6.18 Hz, 6 H), 3.22-3.31 (m, 2 H), 3.45 (s, 3 H), 3.49-3.56 (m, 4 H), 3.61 (dt, J=12.07, 6.04 Hz, 1 H), 4.14 (s, 2 H), 4.29 (t, J=6.32 Hz, 2 H), 7.11-7.19 (m, 2 H), 7.26 (t, J=5.62 Hz, 1 H), 7.39 (dd, J=8.56, 5.48 Hz, 2 H), 8.12 (s, 1 H), 8.53 (s, 1 H), 10.38 (t, J=5.48 Hz, 1 H), 17.12 (s, 1 H); ES+ MS: 501 (M+H+).

後処理

  1. concentrationThe reaction was concentrated in vacuo
  2. additionthe resulting residue was treated with 1N NaHSO4
  3. filtrationThe resulting suspension was filtered
  4. washwashed with EtOH and Et2O
  5. customdried in vacuo

出典と根拠

ORDレコード
ord-d131f7bf148647edb22f2d8b040cb74e
出典データセット
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08691991B2

反応ノート

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