Ethanethiol → 5-Methyl-thiophene-2-carboxylic acid (4-methoxy-7-piperazin-1-yl-benzothiazol-2-yl)-amide

HRID 2308512Notes

Reaction equation

HRID 2308512 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[C:25]3[S:24][C:23]([NH:26][C:27]([C:29]4[S:30][C:31]([CH3:34])=[CH:32][CH:33]=4)=[O:28])=[N:22][C:21]=3[C:20]([O:35][CH3:36])=[CH:19][CH:18]=2)[CH2:13][CH2:12]1)=O)C1C=CC=CC=1.B(F)(F)F.CCOCC.C(S)C>ClCCl>[CH3:36][O:35][C:20]1[C:21]2[N:22]=[C:23]([NH:26][C:27]([C:29]3[S:30][C:31]([CH3:34])=[CH:32][CH:33]=3)=[O:28])[S:24][C:25]=2[C:17]([N:14]2[CH2:13][CH2:12][NH:11][CH2:16][CH2:15]2)=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 8000Boron trifluoride etherateHCID 865849124-{4-Methoxy-2-[(5-methyl-thiophene-2-carbonyl)-amino]-benzothiazol-7-yl}-piperazine-1-carboxylic acid benzyl ester

Product 1

HCID 865849425-Methyl-thiophene-2-carboxylic acid (4-methoxy-7-piperazin-1-yl-benzothiazol-2-yl)-amideYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-{4-methoxy-2-[(5-methyl-thiophene-2-carbonyl)-amino]-benzothiazol-7-yl}-piperazine-1-carboxylic acid benzyl ester (300 mg, 0.57 mmol) in dichloromethane (5 ml) were added boron trifluoride diethyl etherate (0.72 ml, 5.7 mmol) and ethane thiol (1.2 ml, 17 mmol) and the mixture stirred for 36 h. The volatile components are evaporated and the residue codistilled twice with toluene. The residue was dissolved in dichloromethane (25 ml), extracted with 1N aqueous sodium carbonate and the organic phase dryed with Na2SO4. Removal of the solvent and flash chromatography (silica, eluent CH2Cl2/MeOH/aqu. NH4OH 100:10:1) afforded the title compound as light yellow solid (58%), MS: m/e=389 (M+H+).

Workup

  1. customThe volatile components are evaporated
  2. dissolutionThe residue was dissolved in dichloromethane (25 ml)
  3. extractionextracted with 1N aqueous sodium carbonate
  4. customRemoval of the solvent and flash chromatography (silica, eluent CH2Cl2/MeOH/aqu. NH4OH 100:10:1)

Sources & evidence

ORD record
ord-01b3811fab8243a295aac587aa4357cb
Source dataset
uspto-grants-2004_12
Patent number
US06835732B2

Reaction notes

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