4-{5-[(4-Chloro-benzo[b]thiophene-2-carbonyl)-amino]-pyridin-2-yl}-piperazine-1-carboxylic acid tert-butyl ester → 4-Chloro-benzo[b]thiophene-2-carboxylic acid (6-piperazin-1-yl-pyridin-3-yl)-amide

HRID 1645335Notes

Reaction equation

HRID 1645335 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]([C:23]3[S:27][C:26]4[CH:28]=[CH:29][CH:30]=[C:31]([Cl:32])[C:25]=4[CH:24]=3)=[O:22])=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C>ClCCl.C(O)(C(F)(F)F)=O.CCOC(C)=O>[N:11]1([C:14]2[N:15]=[CH:16][C:17]([NH:20][C:21]([C:23]3[S:27][C:26]4[CH:28]=[CH:29][CH:30]=[C:31]([Cl:32])[C:25]=4[CH:24]=3)=[O:22])=[CH:18][CH:19]=2)[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

5

Reactant 1

HCID 462239524-{5-[(4-Chloro-benzo[b]thiophene-2-carbonyl)-amino]-pyridin-2-yl}-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 593651784-Chloro-benzo[b]thiophene-2-carboxylic acid (6-piperazin-1-yl-pyridin-3-yl)-amideYield 85%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-{5-[(4-chloro-benzo[b]thiophene-2-carbonyl)-amino]-pyridin-2-yl}-piperazine-1-carboxylic acid tert-butyl ester (75 mg, 0.16 mmol) in 15 mL of dichloromethane and 5 mL of TFA was stirred at room temperature for 2 hr. The reaction mixture was taken up in 100 mL of EtOAc and washed with 100 mL of 1N NaOH, brine and dried over anhydrous sodium sulfate. The solvent was removed and the residue was triturated with diethyl ether and hexanes (1:1 ratio), followed by filtration, to afford the product 4-chloro-benzo[b]thiophene-2-carboxylic acid (6-piperazin-1-yl-pyridin-3-yl)-amide, (50 mg, 85% yield) as an off white solid. LCMS for C18H17ClN4OS calcd. (m/e) 372, observed 373 (M+H).

Workup

  1. washwashed with 100 mL of 1N NaOH, brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was removed
  4. customthe residue was triturated with diethyl ether and hexanes (1:1 ratio)
  5. filtrationfollowed by filtration

Sources & evidence

ORD record
ord-6e8f4239c5ce4fb5aeffd5cd22090539
Source dataset
uspto-grants-2012_02
Patent number
US08124766B2

Reaction notes

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