Trifluoroacetic acid → HCID 57567399, compound

HRID 74101Notes

Reaction equation

HRID 74101 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-484d7e3e35114215bbab0d94208fc195
Source dataset
uspto-grants-2014_09
Patent number
US08829204B2

Reaction notes

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