Benzoyl chloride, 3-chloro- → (S)-N-[1-(3-Chloro-benzoyl)-6-cyano-1,2,3,4-tetrahydroquinolin-3-yl]-benzenesulfonamide

HRID 1363112Notes

Reaction equation

HRID 1363112 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][S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:16])=[O:15])[CH2:6]2)#[N:2].[Cl:23][C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=1)[C:27](Cl)=[O:28]>>[Cl:23][C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=1)[C: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][S:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH2:8]1)=[O:28]

Participants

3

Reactant 2

HCID 69252Benzoyl chloride, 3-chloro-HCID 66757946(S)-N-(6-Cyano-1,2,3,4-tetrahydro-quinolin-3-yl)-benzenesulfonamide

Product 1

HCID 66757647(S)-N-[1-(3-Chloro-benzoyl)-6-cyano-1,2,3,4-tetrahydroquinolin-3-yl]-benzenesulfonamide

Procedure

The title compound was prepared from 1G and 3-chlorobenzoyl chloride by procedures analogous to those described in Example 160. HPLC; 100% at 6.3 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 452 [M+1]+. Chiral HPLC 100% e.e.; retention time=50.4 min; Conditions: AD (4.6×250 mm); Eluted with 25% isopropanol in hexane for 70 min at 1 mL/min.

Workup

  1. washEluted 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)
  2. washEluted with 25% isopropanol in hexane for 70 min at 1 mL/min.

Sources & evidence

ORD record
ord-1c24e95a157541348b4bae2333017efa
Source dataset
uspto-grants-2011_02
Patent number
US07884113B2

Reaction notes

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