Dichloromethane → 4-{4-[(3RS,4SR)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-piperidin-1-yl]-butyl}-1-[(E)-3-(3,4-dichloro-phenyl)-acryloyl]-[1,4]diazepan-5-one

HRID 1867430Notes

Reaction equation

HRID 1867430 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](/[CH:9]=[CH:10]/[C:11]([N:13]2[CH2:19][CH2:18][C:17](=[O:20])[N:16]([CH2:21][CH2:22][CH2:23][CH2:24]I)[CH2:15][CH2:14]2)=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8].[C:26]([Si:30]([CH3:47])([CH3:46])[O:31][C@H:32]1[C@@H:37]([O:38][Si:39]([C:42]([CH3:45])([CH3:44])[CH3:43])([CH3:41])[CH3:40])[CH2:36][CH2:35][NH:34][CH2:33]1)([CH3:29])([CH3:28])[CH3:27].C(=O)([O-])[O-].[Cs+].[Cs+].C(Cl)Cl>CC(N(C)C)=O>[C:26]([Si:30]([CH3:47])([CH3:46])[O:31][CH:32]1[CH:37]([O:38][Si:39]([C:42]([CH3:45])([CH3:44])[CH3:43])([CH3:41])[CH3:40])[CH2:36][CH2:35][N:34]([CH2:24][CH2:23][CH2:22][CH2:21][N:16]2[C:17](=[O:20])[CH2:18][CH2:19][N:13]([C:11](=[O:12])/[CH:10]=[CH:9]/[C:4]3[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=3)[CH2:14][CH2:15]2)[CH2:33]1)([CH3:29])([CH3:28])[CH3:27]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 684330161-[(E)-3-(3,4-dichloro-phenyl)-acryloyl]-4-(4-iodo-butyl)-[1,4]diazepan-5-oneHCID 131727826(cis)-(Rac)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-piperidine2×

Product 1

HCID 684323104-{4-[(3RS,4SR)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-piperidin-1-yl]-butyl}-1-[(E)-3-(3,4-dichloro-phenyl)-acryloyl]-[1,4]diazepan-5-oneYield 75.1%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A solution of 0.279 g (0.56 mmol) of 1-[(E)-3-(3,4-dichloro-phenyl)-acryloyl]-4-(4-iodo-butyl)-[1,4]diazepan-5-one (example 9B) in 2 ml of DMA was treated with 0.195 ml (0.56 mmol) of (cis)-(rac)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-piperidine (intermediate 25) and 0.184 g (0.56 mmol) of cesium carbonate. After 2.25 h at RT, CH2Cl2 was added, filtrated and evaporated. Purification by catridges, Si-Amine, 50 g, (EtOAc/n-heptane 4:1) gave 0.300 g (75%) of the title compound as light brown foam. MS: 712.6 (MH+, 2Cl).

Workup

  1. filtrationfiltrated
  2. customevaporated
  3. customPurification by catridges, Si-Amine, 50 g, (EtOAc/n-heptane 4:1)

Sources & evidence

ORD record
ord-89abfa7ed8ce4512888edcaf55df7fdd
Source dataset
uspto-grants-2009_12
Patent number
US07632829B2

Reaction notes

Loading…