Trichloroisocyanuric Acid → 8-bromo-1-(oxan-4-yl)-3H-imidazo[4,5-c]quinolin-2-one

HRID 1486921Notes

Reaction equation

HRID 1486921 reaction equation
ClN1[C:7](=[O:8])[N:6](Cl)C(=O)N(Cl)C1=O.[Br:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[N:20]=[CH:19][C:18](C(N)=O)=[C:17]2[NH:27][CH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1.C1CCN2C(=NCCC2)CC1>CO>[Br:13][C:14]1[CH:23]=[CH:22][C:21]2[N:20]=[CH:19][C:18]3[NH:6][C:7](=[O:8])[N:27]([CH:28]4[CH2:29][CH2:30][O:31][CH2:32][CH2:33]4)[C:17]=3[C:16]=2[CH:15]=1

Participants

5

Reactant 3

HCID 6909Trichloroisocyanuric AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 1184987956-Bromo-4-(oxan-4-ylamino)quinoline-3-carboxamide

Product 1

HCID 1185026328-bromo-1-(oxan-4-yl)-3H-imidazo[4,5-c]quinolin-2-oneYield 161.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1,3,5-Trichloro-1,3,5-triazinane-2,4,6-trione (18.9 g, 81.9 mmol) was added portionwise to a mixture of 6-bromo-4-(oxan-4-ylamino)quinoline-3-carboxamide (57.3 g, 163.7 mmol) and DBU (54.7 g, 360.1 mmol) in MeOH (500 mL) at 0° C. The resulting mixture was allowed to warm and stirred at r.t. for 30 minutes. The resulting mixture was evaporated to dryness and the residue triturated with a mixture of petroleum ether/EtOAc (5:1, 1000 mL) to afford the desired material (46.0 g, 81%) as a yellow solid. NMR Spectrum: 1H NMR (400 MHz, DMSO-d6) δ 1.55-1.64 (2H, m), 1.87-1.98 (2H, m), 3.28-3.42 (2H, m), 3.79-3.89 (2H, m), 3.95-3.98 (1H, m), 7.62 (1H, bs), 7.70-7.85 (2H, m), 7.89 (1H, d), 8.12 (1H, bs), 8.60 (1H, s), 8.71 (1H, s).

Workup

  1. temperatureto warm
  2. customThe resulting mixture was evaporated to dryness
  3. customthe residue triturated with a mixture of petroleum ether/EtOAc (5:1, 1000 mL)

Sources & evidence

ORD record
ord-750015ca1b2a4dc7833a21d02de251a1
Source dataset
uspto-grants-2016_08
Patent number
US09428503B2

Reaction notes

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