Triethylamine → HCID 69217711、化合物

反応式

[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:26])[N:8]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)[C:9]2[C:14]([C:15]=1O)=[CH:13][CH:12]=[CH:11][N:10]=2)=[O:5])[CH3:2].C(N(CC)CC)C.O=P(Cl)(Cl)[Cl:36]>>[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:26])[N:8]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)[C:9]2[C:14]([C:15]=1[Cl:36])=[CH:13][CH:12]=[CH:11][N:10]=2)=[O:5])[CH3:2]

参加物

反応物 3

HCID 8471Triethylamine

HCID 24813Phosphorus oxychloride

HCID 59699551HCID 59699551、化合物

生成物 1

HCID 69217711HCID 69217711、化合物収率 95%

実験手順

A solution of 4-hydroxy-1-(4-methoxy-benzyl)-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carboxylic acid ethyl ester (13) (0.40 g, 1.13 mmol) and triethylamine (393 μL, 2.82 mmol) was heated in neat POCl3 at 90° C. for 3 h. The solution was cooled and the excess POCl3 was distilled under vacuum. The residue was suspended in saturated NaHCO3 solution, sonicated briefly and filtered. The solids were dissolved in dichloromethane, washed subsequently by saturated NaHCO3 solution, water and brine. The organic phase was dried over MgSO4 and evaporated to yield 400 mg (95%) of 4-chloro-1-(4-methoxy-benzyl)-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carboxylic acid ethyl ester (14) as white solids. 1H-NMR (DMSO-d6): δ 1.30 (t, J=7.0 Hz, 3H), 3.62 (s, 3H), 4.30 (q, J=7.0 Hz, 2H), 5.47 (s, 2H), 6.81 (d, J=7.7 Hz, 2H), 7.21 (d, J=7.6 Hz, 2H), 7.31 (d, J=7.6 Hz, 1H), 8.40 (dd, J=1.5, 7.5 Hz, 1H), 8.71 (dd, J=1.5, 7.5 Hz, 1H); EIMS: 373 (M+1).

後処理

temperatureThe solution was cooled
distillationthe excess POCl3 was distilled under vacuum
customsonicated briefly
filtrationfiltered
dissolutionThe solids were dissolved in dichloromethane
washwashed subsequently by saturated NaHCO3 solution, water and brine
dry with materialThe organic phase was dried over MgSO4
customevaporated

出典と根拠

ORDレコード: ord-102a2722949b4c77a561e24f2d47cf33
出典データセット: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US07361760B2

反応ノート

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