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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
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HRID 2364386 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][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
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참가 물질

5

반응물 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

생성물 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

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-d131f7bf148647edb22f2d8b040cb74e
출처 데이터셋
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08691991B2

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