2-Oxo-2,3-dihydro-1H-indole-5-carbonitrile → HCID 135544057、化合物

HRID 748533ノート

反応式

HRID 748533 の反応式
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6]2)#[N:2].[Cl:13][C:14]1[CH:15]=[C:16]([CH:26]=[CH:27][N:28]=1)[C:17]([N:19]1[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]1)=[O:18]>>[ClH:13].[OH:12][C:7]1[NH:8][C:9]2[C:5]([C:6]=1[C:27]1[CH:26]=[C:16]([C:17]([N:19]3[CH2:20][CH2:21][N:22]([CH3:25])[CH2:23][CH2:24]3)=[O:18])[CH:15]=[CH:14][N:28]=1)=[CH:4][C:3]([C:1]#[N:2])=[CH:11][CH:10]=2

参加物

3

反応物 2

HCID 27733462-Oxo-2,3-dihydro-1H-indole-5-carbonitrileHCID 252192501-(2-Chloroisonicotinoyl)-4-methylpiperazine

生成物 1

HCID 135544057HCID 135544057、化合物収率 2%

実験手順

The reaction was performed as described in Example 49 using 5-cyanooxindole and 1-(2-chloroisonicotinoyl)-4-methylpiperazine. The crude product was purified on a silica gel column using chloroform/ethanol/conc. NH3(aq), (100:10:1), as the eluent. The base (20 mg) was dissolved in chloroform and a solution of HCl in diethyl ether was added until acidic pH. The formed precipitation was filtered and washed with diethyl ether. Drying in vacuo afforded 10 mg the title compound as a red solid. Yield: 2%: 1H NMR (D2O, 400 MHz) δ 7.82-7.77 (m, 1 H), 7.18-7.11 (m, 1 H), 7.09-7.05 (m, 1 H), 7.04-6.98 (m, 1 H), 6.78-6.71 (m, 1 H), 6.67-6.61 (m, 1 H), 4.05-3.94 (m, 1 H), 3.93-3.82 (m, 1 H), 3.67-3.48 (m, 2 H), 3.48-3.37 (m, 1 H), 3.35-3.04 (m, 3 H), 2.92-2.80 (m, 3 H); MS (TSP) m/s 362 (M++1).

後処理

  1. customThe crude product was purified on a silica gel column
  2. dissolutionThe base (20 mg) was dissolved in chloroform
  3. additiona solution of HCl in diethyl ether was added until acidic pH
  4. customThe formed precipitation
  5. filtrationwas filtered
  6. washwashed with diethyl ether
  7. customDrying in vacuo

出典と根拠

ORDレコード
ord-3f270597c0904e46ba87a2e15c645233
出典データセット
uspto-grants-2008_07
特許番号
US07399780B2

反応ノート

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