HCID 11588147, compound → HCID 11681345, compound

HRID 746608Notes

Reaction equation

HRID 746608 reaction equation
[CH3:1][N:2]([CH3:24])[CH2:3][CH2:4][C:5]1[S:9][C:8]2[CH:10]=[C:11]([CH3:14])[CH:12]=[CH:13][C:7]=2[C:6]=1[C:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)(O)[CH3:16]>C(O)(C(F)(F)F)=O.S(=O)(=O)(O)O>[CH3:24][N:2]([CH3:1])[CH2:3][CH2:4][C:5]1[S:9][C:8]2[CH:10]=[C:11]([CH3:14])[CH:12]=[CH:13][C:7]=2[C:6]=1[C:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)=[CH2:16]

Participants

4

Reactant 1

HCID 11588147HCID 11588147, compound2×

Product 1

HCID 11681345HCID 11681345, compound

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a cooled solution of 1-[2-(2-dimethylamino-ethyl)-6-methyl-benzo[b]thiophen-3-yl]-1-pyridin-2-yl-ethanol (Compound 4-5) (220 mg, 0.65 mmol) in TFA (2 mL), conc. sulfuric acid (500 uL) was added dropwise and the reaction was allowed to warm up to room temperature. After stirring for 4 hours the mixture was concentrated slightly, made basic with 1N NaOH and extracted with EtOAc (4 times). The combined organic layers were washed with brine, dried (Na2SO4), filtered and concentrated. Purification using mass triggered preparative HPLC afforded dimethyl-{2-[6-methyl-3-(1-pyridin-2-yl-vinyl)-benzo[b]thiophen-2-yl]-ethyl}-amine (Compound 4-6). (MH+=323.0, tR=40.15, Method 2)

Workup

  1. concentrationwas concentrated slightly
  2. extractionextracted with EtOAc (4 times)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification

Sources & evidence

ORD record
ord-2bab8529775a4bc2a5da21ceb5e5e1b0
Source dataset
uspto-grants-2008_07
Patent number
US07393865B2

Reaction notes

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