Triphenylphosphine → HCID 3010662, compound

HRID 2229337Notes

Reaction equation

HRID 2229337 reaction equation
N(C(OCC)=O)=NC(OCC)=[O:4].[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[CH:46]=[CH:45][CH:44]=[C:43]2[C:38]=1[CH:39]=[CH:40][CH:41]=[N:42]2.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=C(Cl)C=C(C(OO)=O)C=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[CH:46]=[CH:45][CH:44]=[C:43]5[C:38]=4[CH:39]=[CH:40][CH:41]=[N+:42]5[O-:4])[CH:28]=[N:27][C:21]=3[N:22]([CH2:25][CH3:26])[C:23]=2[N:24]=1

Participants

7

Reactant 5

HCID 11776TriphenylphosphineHCID 70297m-Chloroperbenzoic acidHCID 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 135441757Quinolin-5-ol

Product 1

HCID 3010662HCID 3010662, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Diethyl azodicarboxylate (DEAD) (160 μL, 1.01 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 (225 mg, 0.68 mmol), 5-hydroxyquinoline (147 mg, 1.01 mmol) and Ph3P (266 mg, 1.01 mmol) in THF (3.4 mL) at room temperature. The mixture was stirred at room temperature for 3 h then was concentrated under reduced pressure. The residue was partially purified by flash chromatography (EtOAc:MeOH; 95:5). The fractions containing the 5-quinolinyloxy derivative were concentrated, dissolved in CH2Cl2 (2 mL) and THF (5 mL) and treated with mCPBA (80%, 248 mg, 1.15 mmol) at room temperature. The solution was stirred at room temperature for 2.5 h, then was concentrated under reduced pressure. The residue was dissolved in EtOAc (50 mL), washed successively with aqueous 10% Na2S2O3 (3×10 mL), aqueous saturated NaHCO3 (3×10 mL) and brine (10 mL), then was dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (EtOAc:MeOH, 95:5 to CH2Cl2:MeOH, 9:1) to give the title compound (113 mg, 35% yield for 2 steps) as a white solid: MS (ESI) m/z 476/478 (MH)+.

Workup

  1. concentrationthen was concentrated under reduced pressure
  2. customThe residue was partially purified by flash chromatography (EtOAc:MeOH; 95:5)
  3. additionThe fractions containing the 5-quinolinyloxy derivative
  4. concentrationwere concentrated
  5. dissolutiondissolved in CH2Cl2 (2 mL)
  6. stirringThe solution was stirred at room temperature for 2.5 h
  7. concentrationwas concentrated under reduced pressure
  8. dissolutionThe residue was dissolved in EtOAc (50 mL)
  9. washwashed successively with aqueous 10% Na2S2O3 (3×10 mL), aqueous saturated NaHCO3 (3×10 mL) and brine (10 mL)
  10. dry with materialwas dried (MgSO4)
  11. filtrationfiltered
  12. concentrationconcentrated under reduced pressure
  13. customThe residue was purified by flash chromatography (EtOAc:MeOH, 95:5 to CH2Cl2:MeOH, 9:1)

Sources & evidence

ORD record
ord-24963a2ca1c440318e8a27aa8fe40894
Source dataset
uspto-grants-2002_07
Patent number
US06420359B1

Reaction notes

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