HCID 11702448, compound → HCID 58591574, compound

HRID 746618Notes

Reaction equation

HRID 746618 reaction equation
[CH3:1][N:2]([CH3:21])[CH2:3][CH2:4][C:5]1[S:9][C:8]2[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=2[C:6]=1[C:14]([C:16]1[S:20][CH:19]=[N:18][CH:17]=1)=[O:15].[CH3:22][Mg+].[Br-]>C1COCC1>[CH3:21][N:2]([CH3:1])[CH2:3][CH2:4][C:5]1[S:9][C:8]2[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=2[C:6]=1[C:14]([C:16]1[S:20][CH:19]=[N:18][CH:17]=1)([OH:15])[CH3:22]

Participants

4

Reactant 2

HCID 11702448HCID 11702448, compoundHCID 178418689HCID 178418689, compound2×

Product 1

HCID 58591574HCID 58591574, compoundYield 8.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a cooled (−78° C.) solution of [2-(2-dimethylamino-ethyl)-benzo[b]thiophen-3-yl]-thiazol-5-yl-methanone (35 mg, 0.11 mmol) in anhydrous THF (2 mL), MeMgBr (0.4 mL, 0.55 mmol, 3M in ether) was added. The mixture was stirred for 1 hour at −78° C., an additional batch of MeMgBr (10 mL, 14 mmol) was added and the temperature was allowed to slowly increase to room temperature. The reaction was quenched with diluted NH4OH until pH ˜8, extracted with EtOAc and concentrated. The residue was purified by mass triggered preparative HPLC to give 3 mg of 1-[2-(2-dimethylamino-ethyl)-benzo[b]thiophen-3-yl]-1-thiazol-5-yl-ethanol (Compound 17-1) as a TFA salt.

Workup

  1. additionwas added
  2. temperatureto slowly increase to room temperature
  3. customThe reaction was quenched with diluted NH4OH until pH ˜8
  4. extractionextracted with EtOAc
  5. concentrationconcentrated
  6. customThe residue was purified by mass

Sources & evidence

ORD record
ord-2556e8a8461041b38c400f0b552d8547
Source dataset
uspto-grants-2008_07
Patent number
US07393865B2

Reaction notes

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