Triphenylphosphine → 5-Nitro-8-(2-{[3-(1-piperazinyl)-2-pyrazinyl]oxy}ethoxy)quinoline, Hydrochloride

HRID 493291Notes

Reaction equation

HRID 493291 reaction equation
CCOC(/N=N/C(OCC)=O)=O.C(OC([N:20]1[CH2:25][CH2:24][N:23]([C:26]2[C:27]([O:32][CH2:33][CH2:34][OH:35])=[N:28][CH:29]=[CH:30][N:31]=2)[CH2:22][CH2:21]1)=O)(C)(C)C.O[C:37]1[CH:38]=[CH:39][C:40]([N+:47]([O-:49])=[O:48])=[C:41]2[C:46]=1[N:45]=[CH:44][CH:43]=[CH:42]2.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Cl)[Cl:70].C(O)(C(F)(F)F)=O.O>C1COCC1>[ClH:70].[N+:47]([C:40]1[CH:39]=[CH:38][C:37]([O:35][CH2:34][CH2:33][O:32][C:27]2[C:26]([N:23]3[CH2:22][CH2:21][NH:20][CH2:25][CH2:24]3)=[N:31][CH:30]=[CH:29][N:28]=2)=[C:46]2[C:41]=1[CH:42]=[CH:43][CH:44]=[N:45]2)([O-:49])=[O:48]

Participants

7

Reactant 5

HCID 11776TriphenylphosphineHCID 19910NitroxolineHCID 5462977Diethyl azodicarboxylateHCID 114160742-[3-(4-Tert-butoxycarbonyl-1-piperazinyl)-2-pyrazinyloxy]ethanolHCID 18672661HCID 18672661, compound

Product 1

HCID 1317274445-Nitro-8-(2-{[3-(1-piperazinyl)-2-pyrazinyl]oxy}ethoxy)quinoline, HydrochlorideYield 15%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

DEAD (0.485 mL, 3.08 mmol) was added to a stirred solution of 2-[3-(4-tert-butoxycarbonyl-1piperazinyl)-2-pyrazinyloxy]ethanol (1.00 g, 3.08 mmol; prepared in Example 52, Step 2), 8-hydroxy-5-nitroquinoline (0.589 g, 3.08 mmol) and PPh3 (0.85 g, 3 24 mmol) in THF (10 mL). The mixture was stirred at room temperature for 2 h, and concentrated. The residue was passed through a silica column using toluene/EtOAc (1.1) as eluent The N-Boc protected intermediate obtained was treated with CH2Cl2/TFA/H2O (50:45:5, 15 mL) for 30 min at room temperature and concentrated. The residue was dissolved in 0 1 M aqueous HCl and washed with toluene The water phase was concentrated to give 0.206 g (15%) of the title product. Pos-EI-MS shows M= and 7 ions supporting the stated structure: HRMS m/z calcd for C19H20N6O4 (M)+396.1546, found 396.1557.

Workup

  1. concentrationconcentrated
  2. customobtained
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in 0 1 M aqueous HCl
  5. washwashed with toluene The water phase
  6. concentrationwas concentrated

Sources & evidence

ORD record
ord-48f2b1c48b5b4f9e9ca4cbdaeb7a0399
Source dataset
uspto-grants-2009_05
Patent number
US07534794B2

Reaction notes

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