3-Chlorobenzaldehyde → (S)-1-[1-(3-Chlorobenzyl)-6-cyano-1,2,3,4-tetrahydroquinolin-3-yl]-3-cyclohexylurea

HRID 2234257Notes

Reaction equation

HRID 2234257 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH2:8][C@@H:7]([NH:13][C:14]([NH:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)=[O:15])[CH2:6]2)#[N:2].[Cl:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=1)[CH:27]=O>>[Cl:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=1)[CH2:27][N:9]1[C:10]2[C:5](=[CH:4][C:3]([C:1]#[N:2])=[CH:12][CH:11]=2)[CH2:6][C@H:7]([NH:13][C:14]([NH:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[O:15])[CH2:8]1

Participants

3

Reactant 2

HCID 114773-ChlorobenzaldehydeHCID 68580405(S)-1-[6-Cyano-1,2,3,4-tetrahydroquinolin-3-yl]-3-cyclohexyl-urea

Product 1

HCID 11697505(S)-1-[1-(3-Chlorobenzyl)-6-cyano-1,2,3,4-tetrahydroquinolin-3-yl]-3-cyclohexylurea

Procedure

The title compound was prepared from (S)-1-[6-cyano-1,2,3,4-tetrahydroquinolin-3-yl]-3-cyclohexyl-urea, prepared as described in Example 42A, and 3-chlorobenzaldehyde by procedures analogous to those described in Example 3A. HPLC (method B): retention time=7.50 min. MS (ES): m/z 423 [M+H]+. Chiral HPLC 100% e.e.; retention time=12.2 min; Conditions: AD (4.6×250 mm); Eluted with 20% isopropanol in hexanes for 30 min at 1 mL/min.

Workup

  1. customprepared
  2. washEluted with 20% isopropanol in hexanes for 30 min at 1 mL/min.

Sources & evidence

ORD record
ord-ff0b6b5573844d4bb47f9491ab4e9109
Source dataset
uspto-grants-2010_05
Patent number
US07709647B2

Reaction notes

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