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

HRID 748533Notes

Reaction equation

HRID 748533 reaction equation
[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

Participants

3

Reactant 2

HCID 27733462-Oxo-2,3-dihydro-1H-indole-5-carbonitrileHCID 25219250(2-Chloropyridin-4-yl)(4-methylpiperazin-1-yl)methanone

Product 1

HCID 135544057HCID 135544057, compoundYield 2%

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-3f270597c0904e46ba87a2e15c645233
Source dataset
uspto-grants-2008_07
Patent number
US07399780B2

Reaction notes

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