Triphenylphosphine → 7-chloro-5-[(4-methyl-1-piperazinyl)carbonylmethyl]-1-[2-methoxy-4-[N-[2-(2-methylphenoxy)ethyl]-N-trifluoroacetylamino]benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine

HRID 1870451Notes

Reaction equation

HRID 1870451 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([C:12](=[O:28])[C:13]3[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:25])[C:21]([F:24])([F:23])[F:22])=[CH:15][C:14]=3[O:26][CH3:27])[CH2:10][CH2:9][CH2:8][CH:7]([CH2:29][C:30]([N:32]3[CH2:37][CH2:36][N:35]([CH3:38])[CH2:34][CH2:33]3)=[O:31])[C:6]=2[CH:39]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH2:60][CH2:61][O:62][C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][C:64]=1[CH3:69].N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([C:12](=[O:28])[C:13]3[CH:18]=[CH:17][C:16]([N:19]([CH2:60][CH2:61][O:62][C:63]4[CH:68]=[CH:67][CH:66]=[CH:65][C:64]=4[CH3:69])[C:20](=[O:25])[C:21]([F:24])([F:23])[F:22])=[CH:15][C:14]=3[O:26][CH3:27])[CH2:10][CH2:9][CH2:8][CH:7]([CH2:29][C:30]([N:32]3[CH2:33][CH2:34][N:35]([CH3:38])[CH2:36][CH2:37]3)=[O:31])[C:6]=2[CH:39]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 22539Ethanol, 2-(o-tolyloxy)-HCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 180010547-chloro-5-[(4-methyl-1-piperazinyl)carbonyl-methyl]-1-(2-methoxy-4-trifluoroacetylaminobenzoyl)-2,3,4,5-tetrahydro-1H-benzazepine

Product 1

HCID 180010987-chloro-5-[(4-methyl-1-piperazinyl)carbonylmethyl]-1-[2-methoxy-4-[N-[2-(2-methylphenoxy)ethyl]-N-trifluoroacetylamino]benzoyl]-2,3,4,5-tetrahydro-1H-benzazepineYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 7-chloro-5-[(4-methyl-1-piperazinyl)carbonyl-methyl]-1-(2-methoxy-4-trifluoroacetylaminobenzoyl)-2,3,4,5-tetrahydro-1H-benzazepine (0.4 g) in dry tetrahydrofuran (20 ml) are added triphenyl-phosphine (0.54 g) and o-(2-hydroxyethoxy)toluene (0.29 g) at room temperature. To the mixture is added dropwise a solution of diethyl azodicarboxylate (0.32 ml) in dry tetrahydrofuran (5 ml), and the mixture is stirred at room temperature for 16 hours. To the mixture is added water, and the mixture is extracted with diethyl ether. The ether layer is dried, evaporated to remove the solvent, and the residue is purified by silica gel column chromatography (solvent; dichloromethane:methanol=50:1→30:1) to give 7-chloro-5-[(4-methyl-1-piperazinyl)carbonylmethyl]-1-[2-methoxy-4-{N-[2-(2-methylphenoxy)ethyl]-N-trifluoroacetylamino}benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.46 g) as colorless amorphous.

Workup

  1. extractionthe mixture is extracted with diethyl ether
  2. dry with materialThe ether layer is dried
  3. customevaporated
  4. customto remove the solvent
  5. customthe residue is purified by silica gel column chromatography (solvent; dichloromethane:methanol=50:1→30:1)

Sources & evidence

ORD record
ord-73b9ea8f2cfb40f9842796ef9f2d0a40
Source dataset
uspto-grants-2000_08
Patent number
US06096735

Reaction notes

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