[2-(2-Dimethylamino-ethyl)-benzo[b]thiophen-3-yl]-thiazol-4-yl-methanol → [2-(2-Dimethylamino-ethyl)-benzo[b]thiophen-3-yl]-thiazol-4-yl-methanone

HRID 746615Notes

Reaction equation

HRID 746615 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[CH:14]([C:16]1[N:17]=[CH:18][S:19][CH:20]=1)[OH:15]>C(Cl)(Cl)Cl.O=[Mn]=O>[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[N:17]=[CH:18][S:19][CH:20]=1)=[O:15]

Participants

4

Reactant 1

HCID 11645411[2-(2-Dimethylamino-ethyl)-benzo[b]thiophen-3-yl]-thiazol-4-yl-methanol

Product 1

HCID 11716675[2-(2-Dimethylamino-ethyl)-benzo[b]thiophen-3-yl]-thiazol-4-yl-methanoneYield 85%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6212ChloroformSolvent

Procedure

[2-(2-Dimethylamino-ethyl)-benzo[b]thiophen-3-yl]-thiazol-4-yl-methanol (200 mg, 0.42 mmol) was dissolved in CHCl3 (10 mL) and MnO2 (0.54 g, 3.1 mmol) was added. The reaction mixture was stirred overnight, filtered over celite and washed with dichloromethane and MeOH. Purification by preparative HPLC afforded [2-(2-dimethylamino-ethyl)-benzo[b]thiophen-3-yl]-thiazol-4-yl-methanone (Compound 14-2) (113 mg) as a TFA salt. MH+=316.7

Workup

  1. filtrationfiltered over celite
  2. washwashed with dichloromethane and MeOH
  3. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-7961bf30d233497b80ed8d9ea8abb634
Source dataset
uspto-grants-2008_07
Patent number
US07393865B2

Reaction notes

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