Diisopropylethylamine → 2-Chloro-5-(4-[{1,1-dimethylethyl}oxycarbonyl]-piperazin-1-yl)methyl-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

HRID 2298056Notes

Reaction equation

Br[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([Cl:23])=[C:7]([CH:22]=1)[C:8]([NH:10][CH2:11][C:12]12[CH2:21][CH:16]3[CH2:17][CH:18]([CH2:20][CH:14]([CH2:15]3)[CH2:13]1)[CH2:19]2)=[O:9].[C:24]([O:28][C:29]([N:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1)=[O:30])([CH3:27])([CH3:26])[CH3:25].C(N(C(C)C)CC)(C)C>CN(C)C=O.O>[Cl:23][C:6]1[CH:5]=[CH:4][C:3]([CH2:2][N:34]2[CH2:33][CH2:32][N:31]([C:29]([O:28][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:30])[CH2:36][CH2:35]2)=[CH:22][C:7]=1[C:8]([NH:10][CH2:11][C:12]12[CH2:21][CH:16]3[CH2:15][CH:14]([CH2:20][CH:18]([CH2:17]3)[CH2:19]1)[CH2:13]2)=[O:9]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 5-bromomethyl-2-chloro-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (Example 8b, 0.130 g), 1-tertbutyloxycarbonylpiperazine (0.074 g) and diisopropylethylamine (6.3 ml) in dimethylformamide (3 ml) was heated at 60° C. for 3 h. The mixture was diluted with water (10 ml) and extracted with ethyl acetate (3×10 ml). The organic layer was dried over magnesium sulfate, filtered and the filtrate concentrated under reduced pressure. The crude material was purified on a silica gel eluting with dichloromethane/ethanol (0-20% gradient) to afford the title compound as a white foam (0.112 g).

Workup

extractionextracted with ethyl acetate (3×10 ml)
dry with materialThe organic layer was dried over magnesium sulfate
filtrationfiltered
concentrationthe filtrate concentrated under reduced pressure
customThe crude material was purified on a silica gel eluting with dichloromethane/ethanol (0-20% gradient)

Sources & evidence

ORD record: ord-e927f32908374d0bb6a3dbbdf81fc76f
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06492355B1

Reaction notes

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