m-Formylbenzonitrile → N-(1-(3-Cyanobenzyl)-6-(4-fluorophenyl)-1,2,3,4-tetrahydroquinolin-3-yl)benzenesulfonamide

HRID 1363096Notes

Reaction equation

HRID 1363096 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[NH:14][CH2:13][CH:12]([NH:18][S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)(=[O:21])=[O:20])[CH2:11]3)=[CH:4][CH:3]=1.[C:28]([C:30]1[CH:31]=[C:32]([CH:35]=[CH:36][CH:37]=1)[CH:33]=O)#[N:29].C(N1C2C(=CC(Cl)=CC=2)CC(NC(=O)OC(C)(C)C)C1)C1C=CC=CC=1>>[C:28]([C:30]1[CH:31]=[C:32]([CH:35]=[CH:36][CH:37]=1)[CH2:33][N:14]1[C:15]2[C:10](=[CH:9][C:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)=[CH:17][CH:16]=2)[CH2:11][CH:12]([NH:18][S:19]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)(=[O:20])=[O:21])[CH2:13]1)#[N:29]

Participants

4

Reactant 3

HCID 90670m-FormylbenzonitrileHCID 59297049tert-Butyl 1-benzyl-6-chloro-1,2,3,4-tetrahydroquinolin-3-ylcarbamateHCID 59778193N-(6-(4-Fluorophenyl)-1,2,3,4-tetrahydroquinolin-3-yl)benzene sulfonamide

Product 1

HCID 59778170N-(1-(3-Cyanobenzyl)-6-(4-fluorophenyl)-1,2,3,4-tetrahydroquinolin-3-yl)benzenesulfonamide

Procedure

Compound 113B was prepared from 113A and 3-cyanobenzaldehyde by procedures analogous to those described in 22A. HPLC: 96% at 6.25 min (retention time) (Conditions: Zorbax SB C18 (4.6×75 mm); Eluted with 0% to 100% B, 8 min gradient. (A=90% H2O−10% MeOH−0.1% H3PO4 and B=10% H2O−90% MeOH−0.1% H3PO4); Flow rate at 2.5 mL/min. UV detection at 220 nm). MS (ES): m/z 498 [M+1]+.

Workup

  1. washEluted with 0% to 100% B, 8 min gradient

Sources & evidence

ORD record
ord-e7f286745ca44b6691f3da33b06a714b
Source dataset
uspto-grants-2011_02
Patent number
US07884113B2

Reaction notes

Loading…