Triphenylphosphine → 5,11-Dihydro-11-ethyl-2-fluoro-5-methyl-8{2-(4-quinolinyloxy)ethyl}-6h-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

HRID 2229320Notes

Reaction equation

HRID 2229320 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[CH2:13]([N:15]1[C:21]2[N:22]=[CH:23][C:24]([CH2:26][CH2:27][OH:28])=[CH:25][C:20]=2[C:19](=[O:29])[N:18]([CH3:30])[C:17]2[CH:31]=[CH:32][C:33]([F:35])=[N:34][C:16]1=2)[CH3:14].O[C:37]1[C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[N:40]=[CH:39][CH:38]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1>[CH2:13]([N:15]1[C:21]2[N:22]=[CH:23][C:24]([CH2:26][CH2:27][O:28][C:37]3[C:46]4[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=4)[N:40]=[CH:39][CH:38]=3)=[CH:25][C:20]=2[C:19](=[O:29])[N:18]([CH3:30])[C:17]2[CH:31]=[CH:32][C:33]([F:35])=[N:34][C:16]1=2)[CH3:14]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 112670525,11-Dihydro-11-ethyl-2-fluoro-8-(2-hydroxyethyl)-5-methyl-6H-dipyrido [3,2-b:2',3'-e][1,4]diazepin-6-oneHCID 178516385quinolin-4-ol

Product 1

HCID 30106485,11-Dihydro-11-ethyl-2-fluoro-5-methyl-8{2-(4-quinolinyloxy)ethyl}-6h-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-oneYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethyl azodicarboxylate (DEAD) (14.3 mL, 91.0 mmol) was added drop-wise to a solution of 5,11-dihydro-11-ethyl-2-fluoro-8-(2-hydroxyethyl)-5-methyl-6H-dipyrido[3,2-b:2′,3′-e][1,4]diazepin-6-one (19.2 g, 60.7 mmol), 4-hydroxyquinoline (13.2 g, 91.0 mmol) and Ph3P (23.9 g, 91.0 mmol) in THF (300 mL) at room temperature. The mixture was stirred at room temperature for 1 h then was concentrated under reduced pressure. The residue was purified by flash chromatography (EtOAc:MeOH; 95:5) to give the title compound (17.9 g, 67% yield) as a white solid: MS (ESI) m/z 444 (M)+.

Workup

  1. concentrationthen was concentrated under reduced pressure
  2. customThe residue was purified by flash chromatography (EtOAc:MeOH; 95:5)

Sources & evidence

ORD record
ord-49b2a02d6e7d47d69fe4c0efb6a0a4c1
Source dataset
uspto-grants-2002_07
Patent number
US06420359B1

Reaction notes

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