Triethylamine → HCID 118502860, compound

HRID 1486955Notes

Reaction equation

HRID 1486955 reaction equation
C([N:3]([CH2:6]C)CC)C.[Br:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[CH:14][C:13](C(O)=O)=[C:12]2[NH:22][C@@H:23]1[CH2:27][CH2:26][O:25][CH2:24]1.P(N=[N+]=[N-])(=O)(OC1C=CC=CC=1)[O:29]C1C=CC=CC=1>CN(C=O)C.O>[Br:8][C:9]1[CH:18]=[CH:17][C:16]2[N:15]=[CH:14][C:13]3[NH:3][C:6](=[O:29])[N:22]([C@@H:23]4[CH2:27][CH2:26][O:25][CH2:24]4)[C:12]=3[C:11]=2[CH:10]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 123414Diphenylphosphoryl azideHCID 1185029036-bromo-4-[[(3R)-tetrahydrofuran-3-yl]amino]quinoline-3-carboxylic acid

Product 1

HCID 118502860HCID 118502860, compoundYield 96.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Triethylamine (2.60 ml, 18.69 mmol) was added to 6-bromo-4-[[(3R)-tetrahydrofuran-3-yl]amino]quinoline-3-carboxylic acid (2.1 g, 6.23 mmol) in DMF (30 mL) and the resulting mixture stirred at ambient temperature for 1 h. Diphenyl phosphorazidate (3.43 g, 12.46 mmol) was added and the resulting mixture stirred at 60° C. overnight. The reaction mixture was diluted with water (300 mL) and the solids collected by filtration to afford the desired material as a yellow solid (2.0 g, 96%). NMR Spectrum: 1H NMR (300 MHz, DMSO-d6) δ 2.42-2.45 (2H, m), 3.85-3.90 (1H, m), 4.05-4.16 (2H, m), 4.16-4.25 (1H, m), 5.62-5.72 (1H, m), 7.16-7.18 (1H, m), 7.74 (1H, d), 7.97 (1H, d), 8.68 (1H, s), 8.73 (1H, s), 11.84 (1H, s). Mass Spectrum: m/z (ES+)[M+H]+=334.

Workup

  1. stirringthe resulting mixture stirred at 60° C. overnight
  2. filtrationthe solids collected by filtration

Sources & evidence

ORD record
ord-9a5a605d5f89418a93342438f3b7f637
Source dataset
uspto-grants-2016_08
Patent number
US09428503B2

Reaction notes

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