Sodium Iodide → HCID 21993643, compound

HRID 1978535Notes

Reaction equation

HRID 1978535 reaction equation
[CH2:1](Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.Cl.[O:11]=[C:12]1[CH2:17][NH:16][CH2:15][CH2:14][N:13]1[CH2:18][CH2:19][CH2:20][NH:21][C:22]([C:24]1[S:34][C:33]2[N:35]3[C:26](=[CH:27][N:28]=[C:29]3[CH:30]=[CH:31][CH:32]=2)[CH:25]=1)=[O:23].C(N(CC)CC)C.[I-].[Na+].N12CCCNC1CCCC=C2>C(#N)C>[C:2]1([CH2:1][N:16]2[CH2:15][CH2:14][N:13]([CH2:18][CH2:19][CH2:20][NH:21][C:22]([C:24]3[S:34][C:33]4[N:35]5[C:26](=[CH:27][N:28]=[C:29]5[CH:30]=[CH:31][CH:32]=4)[CH:25]=3)=[O:23])[C:12](=[O:11])[CH2:17]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 7503Benzyl ChlorideHCID 8471TriethylamineHCID 98128211,8-Diazabicyclo[5.4.0]undec-2-eneHCID 21993635HCID 21993635, compound

Product 1

HCID 21993643HCID 21993643, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Benzylchloride (187 mg, 1.48 mmol) was added to a stirred solution of N-[3-(2-oxopiperazin-1-yl)propan-1-yl]-5-thia-1,8b-diazaacenaphtylene-4-carboxamide dihydrochloride (518 mg, 1.20 mmol), triethylamine (605 mg, 5.98 mmol), sodium iodide (216 mg, 1.44 mmol) and 1,8-diazabicyclo[5.4.0]undecene (366 mg, 2.41 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-phenylmethyl-2-oxopiperazine-1-yl)propane-1-yl]-5-thia-1,8b-diazaacenaphthylene-4-carboxamide as a purple amorphous powdeer (303 mg, 56%).

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-b5d4dcbbf3cf47d2b4012f7da435cdaa
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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