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Hydrochloric Acid → 6-(7-Oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-4-yloxy)quinoline-3-carboxylic acid

HRID 1894975
ノート
印刷プレビュー

反応式

HRID 1894975 の反応式
F[C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][C:6](=[O:12])[NH:7]2.[OH:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[N:20]=[CH:19][C:18]([C:24]([OH:26])=[O:25])=[CH:17]2.C(=O)([O-])[O-].[Cs+].[Cs+].Cl>O.CN(C)C=O>[O:12]=[C:6]1[NH:7][C:8]2[N:9]=[CH:10][CH:11]=[C:2]([O:13][C:14]3[CH:15]=[C:16]4[C:21](=[CH:22][CH:23]=3)[N:20]=[CH:19][C:18]([C:24]([OH:26])=[O:25])=[CH:17]4)[C:3]=2[CH2:4][CH2:5]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 468532395-fluoro-3,4-dihydro-1,8-naphthyridin-2(1H)-oneHCID 589024556-Hydroxyquinoline-3-carboxylic acid

生成物 1

HCID 585256386-(7-Oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-4-yloxy)quinoline-3-carboxylic acid

試薬・触媒・溶媒 2

HCID 962
Water
溶媒
HCID 6228Dimethylformamide溶媒

反応条件

温度
150 °C

実験手順

5-fluoro-3,4-dihydro-1,8-naphthyridin-2(1H)-one (Int-28, 120 mg, 0.72 mmol), 6-hydroxyquinoline-3-carboxylic acid (1.5 mg, 0.794 mmol), and cesium carbonate (706 mg, 2.17 mmol) were weighed into a microwave vial. N,N-Dimethylformamide (3.5 mL) was added and the vial was sealed and heated in a microwave at 150° C. for 4 h. The vial was opened and water was added (5 mL). The resulting clear solution was neutralized by the addition of 1N HCl and washed with ethyl acetate. The washed aqueous phase was acidified to pH 3 and pure product was collected by suction filtration. LC-MS: (FA) ES+ 336; 1H NMR (400 MHz, d6-DMSO) δ ppm 13.55 (s, 1H), 10.60 (s, 1H), 9.27 (d, J=2.1 Hz, 1H), 8.94 (d, J=1.9 Hz, 1H), 8.17 (d, J=9.1 Hz, 1H), 8.07-8.02 (m, 1H), 7.85 (d, J=2.7 Hz, 1H), 7.74 (dd, J=9.1, 2.8 Hz, 1H), 6.52 (d, J=5.7 Hz, 1H), 2.92 (t, J=7.7, 7.7 Hz, 2H), 2.54 (dd, J=8.3, 7.1 Hz, 2H).

後処理

  1. customthe vial was sealed
  2. washwashed with ethyl acetate
  3. filtrationwas collected by suction filtration

出典と根拠

ORDレコード
ord-f4faa32bd88f41e898094011fa21f497
出典データセット
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08513421B2

反応ノート

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