Sodium ethoxide → HCID 57780694、化合物

HRID 2076102ノート

反応式

HRID 2076102 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:15][C:16]2[N:25]=[CH:24][C:23]3[CH2:22][CH2:21][CH2:20][CH:19]([O:26]S(C)(=O)=O)[C:18]=3[N:17]=2)[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1.[CH2:31]([O-])C.[Na+]>CO.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:15][C:16]2[N:25]=[CH:24][C:23]3[CH2:22][CH2:21][CH2:20][CH:19]([O:26][CH3:31])[C:18]=3[N:17]=2)[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1

参加物

5

反応物 2

HCID 2723922Sodium ethoxideHCID 57780691HCID 57780691、化合物

生成物 1

HCID 57780694HCID 57780694、化合物収率 31.5%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

To a solution of methanesulfonic acid 2-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenylamino]-5,6,7,8-tetrahydro-quinazolin-8-yl ester (86 mg, 0.2 mmol) in methanol (2 mL) was added sodium ethanolate (17 mg, 0.3 mmol). The reaction was stirred at room temperature over night under nitrogen, heated to reflux for 1 hour. The reaction was diluted with water and extracted twice with ethyl acetate. The combined organic layers were washed with dried over sodium sulfate, filtered and the solvent was removed under reduced pressure. The residue was purified by reversed phase preparative HPLC using a mixture of water containing formic acid and acetonitrile to yield the title compound (23 mg, 28%) as a yellow gum. MS ISP (m/e): 366.2 (100) [(M+H)+]. 1H NMR (CDCl3, 300 MHz): δ (ppm)=8.35 (s, 1H), 8.26 (s, 1H), 7.85 (d, 1H), 7.75 (s, 1H), 7.16 (d, 1H), 7.09 (d, 1H), 6.88 (s, 1H), 4.19 (t, 1H), 3.88 (s, 3H), 3.58 (s, 3H), 2.55-2.80 (m, 2H), 2.33 (s, 3H), 2.15 (m, 1H), 1.72-2.05 (m, 3H).

後処理

  1. temperatureheated
  2. temperatureto reflux for 1 hour
  3. extractionextracted twice with ethyl acetate
  4. washThe combined organic layers were washed
  5. dry with materialwith dried over sodium sulfate
  6. filtrationfiltered
  7. customthe solvent was removed under reduced pressure
  8. customThe residue was purified by reversed phase preparative HPLC
  9. additiona mixture of water
  10. additioncontaining formic acid and acetonitrile

出典と根拠

ORDレコード
ord-e0515302f9e84cf298383d2bdffcb38e
出典データセット
uspto-grants-2011_04
特許番号
US07923450B2

反応ノート

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