Trifluoroacetic acid → HCID 59152452, compound

HRID 423420Notes

Reaction equation

HRID 423420 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH:26]=[CH:25][C:24]4[CH:27]=[C:28]([C:30]5[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=5)[S:29][C:23]=4[C:22]3=[O:37])=[CH:17][N:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Cl:36][C:33]1[CH:32]=[CH:31][C:30]([C:28]2[S:29][C:23]3[C:22](=[O:37])[N:21]([C:18]4[CH:17]=[N:16][C:15]([O:14][CH:11]5[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]5)=[CH:20][CH:19]=4)[CH:26]=[CH:25][C:24]=3[CH:27]=2)=[CH:35][CH:34]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66673291HCID 66673291, compound

Product 1

HCID 59152452HCID 59152452, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Combine 4-{5-[2-(4-chloro-phenyl)-7-oxo-7H-thieno[2,3-c]pyridin-6-yl]-pyridin-2-yloxy}-piperidine-1-carboxylic acid tert-butyl ester (1.67g, 3.10 mmol) with trifluoroacetic acid (2.31 mL, 31.04 mmol) in dichloromethane (20 mL) and stir at RT overnight. Load the mixture onto an SCX column and wash with methanol and dichloromethane. Elute the product with 2M NH3 in methanol and concentrate in vacuo. Chromatograph the residue (silica gel, eluting with 0-10% 2M NH3 in MeOH:dichloromethane) to yield 996 mg (73%) of 2-(4-chloro-phenyl)-6-[6-(piperidin-4-yloxy)-pyridin-3-yl]-6H-thieno[2,3-c]pyridin-7-one. Add ammonium chloride (45 mg, 0.85 mmol) to a solution of the free base (350 mg, 0.80 mmol) in 15 mL of methanol/dichloromethane (1:1) and sonicate the solution until complete dissolution of NH4Cl. Concentrate in vacuo to yield 379 mg (100%) of the title compound. MS/ES m/z (35C1) 438.0 [M+H]+.

Workup

  1. washLoad the mixture onto an SCX column and wash with methanol and dichloromethane
  2. washElute the product with 2M NH3 in methanol
  3. concentrationconcentrate in vacuo
  4. washChromatograph the residue (silica gel, eluting with 0-10% 2M NH3 in MeOH:dichloromethane)

Sources & evidence

ORD record
ord-c28d2441bd184cb4ae95305aa0259808
Source dataset
uspto-grants-2012_01
Patent number
US08101764B2

Reaction notes

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