Trifluoroacetic acid → 3-(2-(4-(1-amino-2-methylpropan-2-yl)phenyl)acetyl)quinolin-4(1H)-one

HRID 74111Notes

Reaction equation

HRID 74111 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]([CH3:31])([C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18](=[O:30])[C:19]2[C:28](=[O:29])[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[NH:21][CH:20]=2)=[CH:13][CH:12]=1)[CH3:10])(C)(C)C.C(O)(C(F)(F)F)=O.[OH-].[Na+]>C(Cl)Cl>[NH2:7][CH2:8][C:9]([C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]([C:19]2[C:28](=[O:29])[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[NH:21][CH:20]=2)=[O:30])=[CH:13][CH:12]=1)([CH3:10])[CH3:31]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 66675698(2-Methyl-2-{4-[2-oxo-2-(4-oxo-1,4-dihydro-quinolin-3-yl)-ethyl]-phenyl}-propyl)-carbamic acid tert-butyl ester

Product 1

HCID 666753983-(2-(4-(1-amino-2-methylpropan-2-yl)phenyl)acetyl)quinolin-4(1H)-oneYield 169.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2-Methyl-2-{4-[2-oxo-2-(4-oxo-1,4-dihydro-quinolin-3-yl)-ethyl]-phenyl}-propyl)-carbamic acid tert-butyl ester (88) (0.50 g, 1.15 mmol), TFA (5 mL) and CH2Cl2 (5 mL) were combined and stirred at room temerpature overnight. The reaction mixture was then neutralized with 1N NaOH. The precipitate was collected via filtration to yield the product 3-(2-(4-(1-amino-2-methylpropan-2-yl)phenyl)acetyl)quinolin-4(1H)-one as a brown solid (651 mg, 91%). HPLC ret. time 2.26 min, 10-99% CH3CN, 5 min run; ESI-MS 336.5 m/z (MH+).

Workup

  1. filtrationThe precipitate was collected via filtration

Sources & evidence

ORD record
ord-42065645fdef4fa29aafdbdf19365027
Source dataset
uspto-grants-2014_09
Patent number
US08829204B2

Reaction notes

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