Sodium Iodide → HCID 58591563, compound

HRID 746619Notes

Reaction equation

HRID 746619 reaction equation
[Na+].[I-].C[Si](Cl)(C)C.[CH3:8][N:9]([CH3:29])[CH2:10][CH2:11][C:12]1[S:16][C:15]2[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=2[C:13]=1[C:21]([C:24]1[S:28][CH:27]=[N:26][CH:25]=1)(O)[CH3:22]>C(#N)C.ClCCl>[CH3:29][N:9]([CH3:8])[CH2:10][CH2:11][C:12]1[S:16][C:15]2[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=2[C:13]=1[CH:21]([C:24]1[S:28][CH:27]=[N:26][CH:25]=1)[CH3:22]

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 58591574HCID 58591574, compound2×

Product 1

HCID 58591563HCID 58591563, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of NaI (24 mg, 0.16 mmol)) and TMSCl (20 uL, 0.16 mmol) in acetonitrile (0.5 mL) was stirred for 15 min at room temperature. A solution of 1-[2-(2-dimethylamino-ethyl)-benzo[b]thiophen-3-yl]-1-thiazol-5-yl-ethanol (Compound 17-1) (3 mg, 0.01 mmol) in dichloromethane (1.3 mL) was added and the reaction was stirred in a sealed vial at 100° C. for 3 hrs. The mixture was quenched with 1M Na2S2O3 until colorless and diluted NH4OH was added until pH ˜8. The product was extracted with EtOAc and the combined organic layers were washed with diluted NH4OH, concentrated and subjected to mass triggered preparative HPLC purification to afford dimethyl-{2-[3-(1-thiazol-5-yl-ethyl)-benzo[b]thiophen-2-yl]-ethyl}-amine (Compound 17-2). MH+=317.0, tR=4.24 min, (Method 2).

Workup

  1. stirringthe reaction was stirred in a sealed vial at 100° C. for 3 hrs
  2. customThe mixture was quenched with 1M Na2S2O3 until colorless and diluted NH4OH
  3. additionwas added until pH ˜8
  4. extractionThe product was extracted with EtOAc
  5. washthe combined organic layers were washed with diluted NH4OH
  6. concentrationconcentrated
  7. customHPLC purification

Sources & evidence

ORD record
ord-c2ea6e51093941f0b244478628b6e268
Source dataset
uspto-grants-2008_07
Patent number
US07393865B2

Reaction notes

Loading…