Sodium Iodide → HCID 21994029, compound

HRID 1978537Notes

Reaction equation

HRID 1978537 reaction equation
Br[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl.Cl.[O:12]=[C:13]1[CH2:18][NH:17][CH2:16][CH2:15][N:14]1[CH2:19][CH2:20][CH2:21][NH:22][C:23]([C:25]1[S:35][C:34]2[N:36]3[C:27](=[CH:28][N:29]=[C:30]3[CH:31]=[CH:32][CH:33]=2)[CH:26]=1)=[O:24].C(N(CC)CC)C.[I-].[Na+].N12CCCNC1CCCC=C2>C(#N)C>[C:4]1([CH2:3][CH2:2][N:17]2[CH2:16][CH2:15][N:14]([CH2:19][CH2:20][CH2:21][NH:22][C:23]([C:25]3[S:35][C:34]4[N:36]5[C:27](=[CH:28][N:29]=[C:30]5[CH:31]=[CH:32][CH:33]=4)[CH:26]=3)=[O:24])[C:13](=[O:12])[CH2:18]2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 7666Phenethyl bromideHCID 8471TriethylamineHCID 98128211,8-Diazabicyclo[5.4.0]undec-2-eneHCID 21993635HCID 21993635, compound

Product 1

HCID 21994029HCID 21994029, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(2-Bromoethyl)benzene (312 mg, 1.68 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 (610 mg, 1.42 mmol), triethylamine (722 mg, 7.13 mmol), sodium iodide (255 mg, 1.70 mmol) and 1,8-diazabicyclo[5.4.0]undecene (438 mg, 2.88 mmol) in acetonitrile (20 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(20 g) with Ethyl acetate-Methanol (8:1) to give N-[3-[4-(2-phenylethan-1-yl)-2-oxopiperazin-1-yl]propan-1-yl]-5-thia-1,8b-diazaacenaphthylene-4-carboxamide as a purple amorphous powder (288 mg, 44%).

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(20 g) with Ethyl acetate-Methanol (8:1)

Sources & evidence

ORD record
ord-c147277a6b6d4ec4933ffa3b07ceb944
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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