Trifluoroacetic acid → HCID 57567399, compound

HRID 423928Notes

Reaction equation

HRID 423928 reaction equation
C(OC([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([CH3:18])([CH3:17])[CH3:16])=[C:11]([NH:19][C:20]([C:22]2[C:31](=[O:32])[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[NH:24][CH:23]=2)=[O:21])[CH:10]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([CH3:18])([CH3:17])[CH3:16])=[C:11]([NH:19][C:20]([C:22]2[C:31](=[O:32])[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[NH:24][CH:23]=2)=[O:21])[CH:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57567271HCID 57567271, compound

Product 1

HCID 57567399HCID 57567399, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of [3-[(4-oxo-1H-quinolin-3-yl)carbonylamino]-4-tert-butyl-phenyl]aminoformic acid tert-butyl ester (353) (33 mg, 0.08 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, N-(5-amino-2-tert-butyl-phenyl)-4-oxo-1H-quinoline-3-carboxamide (260) (15 mg, 56%). 1H NMR (400 MHz, DMSO-d6) δ 13.23 (d, J=6.6 Hz, 1H), 12.20 (s, 1H), 10.22 (br s, 2H), 8.88 (d, J=6.8 Hz, 1H), 8.34 (d, J=7.8 Hz, 1H), 7.86-7.80 (m, 3H), 7.56-7.52 (m, 2H), 7.15 (dd, J=8.5, 2.4 Hz, 1H), 1.46 (s, 9H); HPLC ret. time 2.33 min, 10-99% CH3CN, 5 min run; ESI-MS 336.3 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-90705d02015740c59ac3ff8df1461ac0
Source dataset
uspto-grants-2012_01
Patent number
US08101767B2

Reaction notes

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