Potassium Iodide → HCID 11711303, compound

HRID 1170517Notes

Reaction equation

HRID 1170517 reaction equation
Cl.[O:2]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][NH+:12]([CH2:14][CH2:15]Cl)[CH3:13])=[CH:10][C:5]=2[O:4][CH2:3]1.[N:17]1([C:22]2[N:26]=[C:25]([CH:27]3[CH2:31][CH2:30][CH2:29][NH:28]3)[S:24][N:23]=2)[CH:21]=[CH:20][N:19]=[CH:18]1.[I-].[K+].OP([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[O:2]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][N:12]([CH2:14][CH2:15][N:28]3[CH2:29][CH2:30][CH2:31][CH:27]3[C:25]3[S:24][N:23]=[C:22]([N:17]4[CH:21]=[CH:20][N:19]=[CH:18]4)[N:26]=3)[CH3:13])=[CH:10][C:5]=2[O:4][CH2:3]1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 24450Potassium Phosphate, DibasicHCID 58654398HCID 58654398, compoundHCID 86605234HCID 86605234, compound

Product 1

HCID 11711303HCID 11711303, compoundYield 4.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of benzo[1,3]dioxol-5-ylmethyl-(2-chloro-ethyl)-methyl-ammonium hydrochloride (130 mg, 492 μmol), 3-imidazol-1-yl-5-pyrrolidin-2-yl-[1,2,4]thiadiazole (110 mg, 497 μmol), potassium iodide (20 mg, 120 μmol), and TEA (200 μL, 1.44 mmol) in DMF (1.8 mL) was heated at 140 C for 7 min. The reaction mixture was cooled to r.t. and poured into 10 mL of 1N K2HPO4(aq)/EtOAc (1:1). The organic layer was isolated and concentrated to crude residue. Purification was achieved using reverse phase HPLC (5% to 100% Acetonitrile/H2O, 0.1% TFA) to afford 10 mg (4%) of benzo[1,3]dioxol-5-ylmethyl-{2-[2-(3-imidazol-1-yl-[1,2,4]thiadiazol-5-yl)-pyrrolidin-1-yl]-ethyl}-methyl-amine as the TFA salt. [M+H]+ 412.85; 1H NMR (400 MHz, CDCl3) δ 9.23 (s, 1H), 7.95 (s, 1H), 7.46 (s, 1H), 6.88 (s, 1H), 6.81 (m, 2H), 6.01 (s, 2H), 4.24 (m, 1H), 4.15 (m, 2H), 3.0-3.4 (m, 5H), 2.72 (s, 3H), 2.58 (m, 1H), 2.40 (m, 1H), 1.98 (m, 2H), 1.90 (m, 1H).

Workup

  1. customThe organic layer was isolated
  2. concentrationconcentrated to crude residue
  3. customPurification

Sources & evidence

ORD record
ord-869fbebca0dd42b7aaf0f18ac6ee1ff8
Source dataset
uspto-grants-2010_11
Patent number
US07825256B2

Reaction notes

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