Sodium hydride → HCID 135440206, compound

HRID 2245560Notes

Reaction equation

HRID 2245560 reaction equation
[H-].[Na+].[Cl:3][C:4]1[N:9]=[CH:8][C:7]([S:10]([N:13]2[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][N:21]([CH2:25][CH2:26][CH3:27])[CH2:22][CH2:23][CH3:24])[CH2:15][CH2:14]2)(=[O:12])=[O:11])=[CH:6][CH:5]=1.[O:28]=[C:29]1[CH2:37][C:36]2[C:31](=[CH:32][C:33]([C:38]#[N:39])=[CH:34][CH:35]=2)[NH:30]1.C(=O)([O-])O.[Na+]>CN1CCCC1=O>[ClH:3].[CH2:22]([N:21]([CH2:25][CH2:26][CH3:27])[CH2:20][CH2:19][N:16]1[CH2:17][CH2:18][N:13]([S:10]([C:7]2[CH:6]=[CH:5][C:4]([C:37]3[C:36]4[C:31](=[CH:32][C:33]([C:38]#[N:39])=[CH:34][CH:35]=4)[NH:30][C:29]=3[OH:28])=[N:9][CH:8]=2)(=[O:12])=[O:11])[CH2:14][CH2:15]1)[CH2:23][CH3:24]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 27733482-Oxindole-6-carbonitrileHCID 11269268HCID 11269268, compound

Product 1

HCID 135440206HCID 135440206, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a suspension of sodium hydride (97%, 0.024 g, 1.0 mmol) in 1-methyl-2-pyrrolidinone (1.5 mL) was added (2-{4-[(6-chloropyridin-3-yl)sulfonyl]piperzin-1-yl}ethyl)dipropylamine (0.194 g, 0.5 mmol) at room temperature followed by addition of 2-oxoindoline-6-carbonitrile (0.095 g, 0.6 mmol). The formed mixture was stirred for 5 min under an N2 atmosphere and stirred for 1 h at 90° C. The cooled solution was poured into a cold saturated aqueous sodium hydrogen carbonate solution and the resulting precipitate was collected by filtration. The crude product was purified on a silica gel column using chloroform/methanol/triethylamine, (100:80:1), as the eluent to give 0.130 g (51% yield) of the title compound as the base. The base (0.127 g, 0.25 mmol) was dissolved in chloroform/methanol, (1:1), and treated with HCl in diethyl ether (1 M) at 0° C. The resulting orange crystals were collected by filtration and washed with diethyl ether to obtain 0.125 g (86% yield) of the title compound: 1H NMR (DMSO-d6, 400 MHz) δ 11.07 (s, 1H), 8.67 (s, 1H), 7.89 (s, 2H), 7.78 (d, J=8.0 Hz, 1H), 7.44 (dd, J=8.0, 1.2 Hz, 1H), 7.28 (d, J=1.2 Hz, 1H), 4.04 (br s, 10H), 3.05 (br s, 6H), 1.69 (br s, 4H), 0.91 (t, J=7.2 Hz, 6H); MS (EI) m/z 511 (M++1).

Workup

  1. stirringstirred for 1 h at 90° C
  2. filtrationthe resulting precipitate was collected by filtration
  3. customThe crude product was purified on a silica gel column

Sources & evidence

ORD record
ord-06164ea3bdab4b0eaa513fd85e4ec751
Source dataset
uspto-grants-2010_03
Patent number
US07683067B2

Reaction notes

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