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

HRID 711674Notes

Reaction equation

HRID 711674 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-e1eac37a3df94ad1aeecc1b442514e82
Source dataset
uspto-grants-2015_11
Patent number
US09181276B2

Reaction notes

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