Sodium Hydroxide → HCID 67416092、化合物

HRID 2193014ノート

反応式

HRID 2193014 の反応式
Cl[C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]1[CH:27]=[N:26][CH:25]=[CH:24][C:5]=1[C:6]([CH2:12][S:13]([N:16]([CH3:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:15])=[O:14])=[N:7]2.[OH-:28].[Na+]>C(O)(=O)C.O>[CH3:23][N:16]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[S:13]([CH2:12][C:6]1[C:5]2[CH:24]=[CH:25][N:26]=[CH:27][C:4]=2[C:3]2[C:2](=[O:28])[NH:11][CH:10]=[CH:9][C:8]=2[N:7]=1)(=[O:14])=[O:15]

参加物

5

反応物 2

HCID 14798Sodium HydroxideHCID 59375562HCID 59375562、化合物

生成物 1

HCID 67416092HCID 67416092、化合物

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

A mixture of 1-(1-chloropyrido[4,3-c]-1,6-naphthyridin-6-yl)-N-methyl-N-phenylmethanesulfonamide (45 mg, 0.113 mmol) in acetic acid (2790 μl) and water (1196 μl) was heated to 100° C. and stirred for 2 h. After cooling to room temperature, the reaction mixture was added to aqueous sodium hydroxide (1M). The aqueous layer was extracted with ethyl acetate. The combined organic extracts were dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by preparative HPLC Reverse phase (C-18), eluting with Acetonitrile/Water+0.05% TFA, to afford N-methyl-1-(1-oxo-1,2-dihydropyrido[4,3-c]-1,6-naphthyridin-6-yl)-N-phenylmethanesulfonamide as a yellow solid. 1H NMR (500 MHz, C2D6SO) δ 12.17 (s, 1H), 11.19 (s, 1H), 8.87 (d, 1H), 8.30 (d, 1H), 7.71 (t, 1H), 7.48 (d, 2H), 7.38 (t, 2H), 7.29 (t, 1H), 6.95 (d, 1H), 5.36 (s, 2H), 3.22 (s, 3H). LRMS (APCI) calc'd for (C14H14N3O) [M+H]+, 381.1; found 381.0.

後処理

  1. temperatureAfter cooling to room temperature
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. dry with materialThe combined organic extracts were dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by preparative HPLC Reverse phase (C-18)
  6. washeluting with Acetonitrile/Water+0.05% TFA

出典と根拠

ORDレコード
ord-35eeaca40656457baafc6b1db5eaae63
出典データセット
uspto-grants-2012_12
特許番号
US08329722B2

反応ノート

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