Triethylamine → (S)-8-bromo-1-(2-methoxypropyl)-1H-imidazo[4,5-c]quinolin-2(3H)-one

HRID 244597Notes

Reaction equation

HRID 244597 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6](C(O)=O)=[C:5]2[NH:15][CH2:16][C@@H:17]([O:19][CH3:20])[CH3:18].C([N:23]([CH2:26]C)CC)C.C1C=CC([O:34]P(OC2C=CC=CC=2)(N=[N+]=[N-])=O)=CC=1>CN(C)C=O.O>[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[NH:23][C:26](=[O:34])[N:15]([CH2:16][C@@H:17]([O:19][CH3:20])[CH3:18])[C:5]=3[C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 123414Diphenylphosphoryl azideHCID 681075623-Quinolinecarboxylic acid, 6-bromo-4-(((2S)-2-methoxypropyl)amino)-

Product 1

HCID 68108183(S)-8-bromo-1-(2-methoxypropyl)-1H-imidazo[4,5-c]quinolin-2(3H)-oneYield 88.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Suspend 6-bromo-4-[[(2S)-2-methoxypropyl]amino]quinoline-3-carboxylic acid (510 g, 1.5 mol) in dimethylformamide (7.65 L) and add triethylamine (419 mL, 3 mol, 2 eq.) at 70° C. Add diphenylphosphonic azide (390 mL, 1.8 mol., 1.2 eq.) dropwise over 30 minutes. Heat the mixture to 70° C. (internal temperature) for 1 hour. Cool to 10° C. and dilute with water (5 L). Stir the mixture for 1 hour, filter the precipitate, wash it with water (2×1 L) and methyl tert-butyl ether (2×1 L), and then let it dry to give the titled compound as a white solid (445 g, 88%). MS (ESI) m/z (M+H)+ 335.9, 337.9.

Workup

  1. temperatureCool to 10° C.
  2. filtrationfilter the precipitate
  3. washwash it with water (2×1 L) and methyl tert-butyl ether (2×1 L)
  4. customdry

Sources & evidence

ORD record
ord-7075bc14a8cd403ea3bee6554708f981
Source dataset
uspto-grants-2014_02
Patent number
US08658668B2

Reaction notes

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