N-[3-(3-butyl-7-dimethylamino-3-ethyl-4-hydroxy-1,1-dioxo-2,3,4,5-tetrahydro-1H-benzo[b]thiepin-5-yl)phenyl]-5-bromopentanamide → N-[3-(3-Butyl-7-dimethylamino-3-ethyl-4-hydroxy-1,1-dioxo-2,3,4,5-tetrahydro-1H-benzo[b]thiepin-5-yl)-phenyl]-5-{4-[3-(3-hydroxy-3-phenylpropyl)-2-(4-methoxyphenyl)-4-oxoazetidin-1-yl]benzylamino}pentanamide

HRID 2300700Notes

Reaction equation

HRID 2300700 reaction equation
[CH2:1]([C:5]1([CH2:36][CH3:37])[CH2:11][S:10](=[O:13])(=[O:12])[C:9]2[CH:14]=[CH:15][C:16]([N:18]([CH3:20])[CH3:19])=[CH:17][C:8]=2[CH:7]([C:21]2[CH:22]=[C:23]([NH:27][C:28](=[O:34])[CH2:29][CH2:30][CH2:31][CH2:32]Br)[CH:24]=[CH:25][CH:26]=2)[CH:6]1[OH:35])[CH2:2][CH2:3][CH3:4].[NH2:38][CH2:39][C:40]1[CH:45]=[CH:44][C:43]([N:46]2[CH:49]([C:50]3[CH:55]=[CH:54][C:53]([O:56][CH3:57])=[CH:52][CH:51]=3)[CH:48]([CH2:58][CH2:59][CH:60]([OH:67])[C:61]3[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=3)[C:47]2=[O:68])=[CH:42][CH:41]=1>CN(C)C=O>[CH2:1]([C:5]1([CH2:36][CH3:37])[CH2:11][S:10](=[O:13])(=[O:12])[C:9]2[CH:14]=[CH:15][C:16]([N:18]([CH3:20])[CH3:19])=[CH:17][C:8]=2[CH:7]([C:21]2[CH:22]=[C:23]([NH:27][C:28](=[O:34])[CH2:29][CH2:30][CH2:31][CH2:32][NH:38][CH2:39][C:40]3[CH:45]=[CH:44][C:43]([N:46]4[C:47](=[O:68])[CH:48]([CH2:58][CH2:59][CH:60]([OH:67])[C:61]5[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=5)[CH:49]4[C:50]4[CH:51]=[CH:52][C:53]([O:56][CH3:57])=[CH:54][CH:55]=4)=[CH:42][CH:41]=3)[CH:24]=[CH:25][CH:26]=2)[CH:6]1[OH:35])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 15922485N-[3-(3-butyl-7-dimethylamino-3-ethyl-4-hydroxy-1,1-dioxo-2,3,4,5-tetrahydro-1H-benzo[b]thiepin-5-yl)phenyl]-5-bromopentanamideHCID 159224861-(4-Aminomethylphenyl)-3-(3-hydroxy-3-phenylpropyl)-4-(4-methoxyphenyl)azetidin-2-one

Product 1

HCID 10213227N-[3-(3-Butyl-7-dimethylamino-3-ethyl-4-hydroxy-1,1-dioxo-2,3,4,5-tetrahydro-1H-benzo[b]thiepin-5-yl)-phenyl]-5-{4-[3-(3-hydroxy-3-phenylpropyl)-2-(4-methoxyphenyl)-4-oxoazetidin-1-yl]benzylamino}pentanamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

100 mg of N-[3-(3-butyl-7-dimethylamino-3-ethyl-4-hydroxy-1,1-dioxo-2,3,4,5-tetrahydro-1H-benzo[b]thiepin-5-yl)phenyl]-5-bromopentanamide and 70 mg of 1-(4-aminomethylphenyl)-3-(3-hydroxy-3-phenylpropyl)-4-(4-methoxyphenyl)azetidin-2-one are dissolved in 5 ml of dimethylformamide and, with stirring, heated at 80° C. for about 2 to 3 hours. After the reaction has ended (monitored by thin-layer chromatogram or HPLC-MS), the solvent is removed under reduced pressure and the residue is purified by chromatography. This gives product 1 of molecular weight 929.24 (C55H68N4O7S); MS (FAB): 929 (M+H+).

Workup

  1. customthe solvent is removed under reduced pressure
  2. customthe residue is purified by chromatography

Sources & evidence

ORD record
ord-dc6b685612354509bb10fb8c79d3d248
Source dataset
uspto-grants-2002_12
Patent number
US06498156B2

Reaction notes

Loading…