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

HRID 44405Notes

Reaction equation

HRID 44405 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) δ7.18 (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-51f20a429bcd4dc89e76bfc3caf41ef4
Source dataset
uspto-grants-2013_09
Patent number
US08541421B2

Reaction notes

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