Sodium Iodide → HCID 21993932, compound

HRID 1978539Notes

Reaction equation

HRID 1978539 reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.Cl.Cl.[O:13]=[C:14]1[CH2:19][NH:18][CH2:17][CH2:16][N:15]1[CH2:20][CH2:21][CH2:22][NH:23][C:24]([C:26]1[S:36][C:35]2[N:37]3[C:28](=[CH:29][N:30]=[C:31]3[CH:32]=[CH:33][CH:34]=2)[CH:27]=1)=[O:25].C(N(CC)CC)C.[I-].[Na+].N12CCCNC1CCCC=C2>C(#N)C>[C:5]1([CH2:4][CH2:3][CH2:2][N:18]2[CH2:17][CH2:16][N:15]([CH2:20][CH2:21][CH2:22][NH:23][C:24]([C:26]3[S:36][C:35]4[N:37]5[C:28](=[CH:29][N:30]=[C:31]5[CH:32]=[CH:33][CH:34]=4)[CH:27]=3)=[O:25])[C:14](=[O:13])[CH2:19]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 12503(3-Bromopropyl)benzeneHCID 98128211,8-Diazabicyclo[5.4.0]undec-2-eneHCID 21993635HCID 21993635, compound

Product 1

HCID 21993932HCID 21993932, compoundYield 66.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-Bromo-3-phenylpropane (210 mg, 1.05 mmol) was added to a stirred solution of N-[3-(2-oxopiperazin-1-yl)propan-1-yl]-5-thia-1,8b-diazaacenaphthylene-4-carboxamide dihydrochloride (389 mg, 0.904 mmol), triethylamine (459 mg, 4.53 mmol), sodium iodide (163 mg, 1.09 mmol) and 1,8-diazabicyclo[5.4.0]undecene (275 mg, 1.81 mmol) in acetonitrile (10 ml) at room temperature. After refluxing under nitrogen for 2 days, the reaction mixture was concentrated in vacuo. The residue was dissolved in water and extracted with chloroform. The extract was washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was chromatographed on silica gel (15 g) with Ethyl acetate-Methanol (8:1) to give N-[3-[4-(3-phenylpropan-1-yl)-2-oxopiperazin-1-yl]propan-1-yl]-5-thia-1,8b-diazaacenaphthylene-4-carboxamide as a purple amorphous powder(285 mg, 66%).

Workup

  1. temperatureAfter refluxing under nitrogen for 2 days
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. dissolutionThe residue was dissolved in water
  4. extractionextracted with chloroform
  5. washThe extract was washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was chromatographed on silica gel (15 g) with Ethyl acetate-Methanol (8:1)

Sources & evidence

ORD record
ord-4935ed95bdf14614b750cfa8732528dd
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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