Triphenylphosphine → HCID 10302036, compound

HRID 394082Notes

Reaction equation

HRID 394082 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[Cl:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:15]=1[N:21]1[C:30]2[C:25](=[C:26]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[Cl:38])[CH:27]=[C:28]([OH:31])[CH:29]=2)[CH2:24][NH:23][C:22]1=[O:39].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH2:60][CH2:61][N:62]1[CH2:67][CH2:66][CH2:65][CH2:64][CH2:63]1>O1CCCC1>[Cl:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:15]=1[N:21]1[C:30]2[C:25](=[C:26]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[Cl:38])[CH:27]=[C:28]([O:31][CH2:60][CH2:61][N:62]3[CH2:67][CH2:66][CH2:65][CH2:64][CH2:63]3)[CH:29]=2)[CH2:24][NH:23][C:22]1=[O:39]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 18232N-PiperidinoethanolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 22647873HCID 22647873, compound

Product 1

HCID 10302036HCID 10302036, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethyl azodicarboxylate (50 μL, 0.32 mmol) was added dropwise to a solution of 1-(2,6dichlorophenyl)-5-(2-chlorophenyl)-7-hydroxy-3,4-dihydro-2(1H)-quinazolinone (30 mg, 0.07 mmol) INTERMEDIATE 49), triphenylphosphine (95 mg, 0.36 mmol) and 1-(2-hydroxyethyl)piperidine (55 mg, 0.43 mmol) in 1 mL tetrahydrofuran at 65° C. under an argon atmosphere. After 1 h the solution was cooled to RT and partitioned between saturated NaHCO3 (5 mL) and EtOAc (15 mL). The organic phase was separated, dried over Na2SO4, filtered and concentrated. The residue was purified by thin layer chromatography using EtOAc followed by CHCl3/MeOH/NH4OH (87/12/1) as the eluent to give 1-(2,6-dichlorophenyl)-5-(2-chlorophenyl)-7-[2-(1-piperidinyl)ethoxy]-3,4-dihydro-2(1H)-quinazolinone. 1H NMR(CDCl3, 500 MHz): δ 1.44 (m, 2H), 1.62 (m, 4H), 2.48 (m, 4H), 2.72 (m, 2H), 4.00 (t, 2H, J=6.0 Hz), 4.18 (d, 1H, J=14.0 Hz), 4.36 (d, 1H, J-14.0 Hz), 5.22 (s, 1H), 5.76 (d, 1H, J=1.8 Hz), 6.45 (d, 1H, J=2.0 Hz), 7.28-7.39 (m, 4H), 7.45-7.53 (m, 3H). MS(ES) 530 (M+H); LC 1: 2.28 min.

Workup

  1. custompartitioned between saturated NaHCO3 (5 mL) and EtOAc (15 mL)
  2. customThe organic phase was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by thin layer chromatography

Sources & evidence

ORD record
ord-39a501b558e3444095463b0ceb0c63f9
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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