N,N-bis(4-methoxybenzyl)-4-(4-methoxybenzylamino)-2-oxo-1,2-dihydroquinoline-3-carboxamide → HCID 25216403, compound

HRID 2077020Notes

Reaction equation

HRID 2077020 reaction equation
COC1C=CC(C[N:8](CC2C=CC(OC)=CC=2)[C:9]([C:11]2[C:12](=[O:31])[NH:13][C:14]3[C:19]([C:20]=2[NH:21]CC2C=CC(OC)=CC=2)=[CH:18][CH:17]=[CH:16][CH:15]=3)=[O:10])=CC=1>C(O)(C(F)(F)F)=O>[NH2:21][C:20]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][C:12](=[O:31])[C:11]=1[C:9]([NH2:8])=[O:10]

Participants

3

Reactant 1

HCID 67097809N,N-bis(4-methoxybenzyl)-4-(4-methoxybenzylamino)-2-oxo-1,2-dihydroquinoline-3-carboxamide

Product 1

HCID 25216403HCID 25216403, compoundYield 249.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

N,N-bis(4-methoxybenzyl)-4-(4-methoxybenzylamino)-2-oxo-1,2-dihydroquinoline-3-carboxamide (Example 74a) (2.0 g, 3.55 mmol) was dissolved in TFA (15 mL) and the solution was stirred at room temperature for 6 hours. The TFA was removed under vacuum, and the resultant solid was stirred in water overnight, then collected by filtration to give 1.8 grams of crude final product. 1H NMR (400 MHz, DMSO-d6) δ 7.18 (m, 2H), 7.25 (d, J=7.2 Hz, 1H), 7.56 (t, J=8.0 Hz, 1H), 8.09 (d, J=7.6 Hz, 2H), 9.83 (d, J=4.8 Hz, 1H), 10.85 (bs, 1H), 11.12 (s, 1H). MS 204 (MH+).

Workup

  1. customThe TFA was removed under vacuum
  2. stirringthe resultant solid was stirred in water overnight
  3. filtrationcollected by filtration

Sources & evidence

ORD record
ord-1b7b7f826ceb4a3faa9fe8f800e96e58
Source dataset
uspto-grants-2011_04
Patent number
US07928111B2

Reaction notes

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