2-Oxo-2,3-dihydro-1H-indole-5-carbonitrile → HCID 135544057, 화합물

HRID 748533노트

반응식

HRID 748533 반응식
[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

참가 물질

3

반응물 2

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

생성물 1

HCID 135544057HCID 135544057, 화합물수율 2%

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-3f270597c0904e46ba87a2e15c645233
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07399780B2

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