Triphenylphosphine → HCID 3010646, compound

HRID 2229310Notes

Reaction equation

HRID 2229310 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[Cl:13][C:14]1[CH:15]=[CH:16][C:17]2[N:18]([CH3:35])[C:19](=[O:34])[C:20]3[CH:30]=[C:29]([CH2:31][CH2:32][OH:33])[CH:28]=[N:27][C:21]=3[N:22]([CH2:25][CH3:26])[C:23]=2[N:24]=1.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>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]2[N:18]([CH3:35])[C:19](=[O:34])[C:20]3[CH:30]=[C:29]([CH2:31][CH2:32][O:33][C:37]4[C:46]5[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=5)[N:40]=[CH:39][CH:38]=4)[CH:28]=[N:27][C:21]=3[N:22]([CH2:25][CH3:26])[C:23]=2[N:24]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 114048102-chloro-5,11-dihydro-11-ethyl-8-(beta-hydroxy)ethyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-oneHCID 178516385quinolin-4-ol

Product 1

HCID 3010646HCID 3010646, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethyl azodicarboxylate (DEAD) (4.26 mL, 27.0 mmol) was added drop-wise to a solution of 2-chloro-5,11-dihydro-11-ethyl-8-(2-hydroxyethyl)-5-methyl-6H-dipyrido[3,2-b:2′,3′-e][1,4]diazepin-6-one (6.00 g, 18.0 mmol), 4-hydroxyquinoline (3.92 g, 27.0 mmol) and Ph3P (7.09 g, 27.0 mmol) in THF (90 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 (6.22 g, 75% yield) as a white solid: MS (ESI) m/z 460/462.

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-dca79012d1ca4d0a89e97c5092c4879a
Source dataset
uspto-grants-2002_07
Patent number
US06420359B1

Reaction notes

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