Trifluoroacetic acid → HCID 57567405, compound

HRID 423935Notes

Reaction equation

HRID 423935 reaction equation
C(OC([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([NH:18][C:19]([C:21]3[C:30](=[O:31])[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[NH:23][CH:22]=3)=[O:20])[CH:16]=2)[CH2:11][CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[O:31]=[C:30]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[NH:23][CH:22]=[C:21]1[C:19]([NH:18][C:15]1[CH:16]=[C:17]2[C:12]([CH2:11][CH2:10][CH2:9][NH:8]2)=[CH:13][CH:14]=1)=[O:20]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57567361HCID 57567361, compound

Product 1

HCID 57567405HCID 57567405, compoundYield 43.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 7-[(4-oxo-1H-quinolin-3-yl)carbonylamino]-1,2,3,4-tetrahydroquinoline-1-carboxylic acid tert-butyl ester (183) (23 mg, 0.05 mmol), TFA (1 mL) and CH2Cl2 (1 mL) was stirred at room temperature overnight. The solution was concentrated and the residue was dissolved in DMSO (1 mL) and purified by HPLC (10-99% CH3CN—H2O) to yield the product, 4-oxo-N-(1,2,3,4-tetrahydroquinolin-7-yl)-1H-quinoline-3-carboxamide (299) (7 mg, 32%). HPLC ret. time 2.18 min, 10-99% CH3CN, 5 min run; ESI-MS 320.3 m/z (MH+).

Workup

  1. concentrationThe solution was concentrated
  2. dissolutionthe residue was dissolved in DMSO (1 mL)
  3. custompurified by HPLC (10-99% CH3CN—H2O)

Sources & evidence

ORD record
ord-a2b8d5dcd8544f10aaa195e581fb3c26
Source dataset
uspto-grants-2012_01
Patent number
US08101767B2

Reaction notes

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