Dimethylformamide → HCID 46853019, compound

HRID 1621323Notes

Reaction equation

HRID 1621323 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][OH:19])=[CH:12][CH:11]=2)[C:5]([C:20]#[N:21])=[C:4]([S:22][CH2:23][C:24]2[N:25]=[C:26]([C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=3)[S:27][CH:28]=2)[N:3]=1.CS(N)(=O)=O.[CH3:41][N:42](C=O)[CH3:43]>>[Cl:35][C:32]1[CH:31]=[CH:30][C:29]([C:26]2[S:27][CH:28]=[C:24]([CH2:23][S:22][C:4]3[C:5]([C:20]#[N:21])=[C:6]([C:10]4[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][OH:19])=[CH:12][CH:11]=4)[C:7]([C:8]#[N:9])=[C:2]([N:42]([CH3:43])[CH3:41])[N:3]=3)[N:25]=2)=[CH:34][CH:33]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 72879MethanesulfonamideHCID 866438472-Chloro-6-({(2-(4-chlorophenyl)-1,3-thiazol-4-yl)methyl}sulfanyl)-4-(4-(2-hydroxyethoxy)phenyl)pyridine-3,5-dicarbonitrile

Product 1

HCID 46853019HCID 46853019, compound

Procedure

At 100° C., 80 mg (0.15 mmol) of 2-chloro-6-({(2-(4-chlorophenyl)-1,3-thiazol-4-yl)methyl}sulfanyl)-4-(4-(2-hydroxyethoxy)phenyl)pyridine-3,5-dicarbonitrile (Example 2A) and 28 mg (0.30 mmol) of methanesulfonamide were stirred in 1.5 ml of DMF overnight. After cooling, the crude product was purified by preparative HPLC (acetonitrile/water). This gave 41 mg (50% of theory) of the target compound.

Workup

  1. temperatureAfter cooling
  2. customthe crude product was purified by preparative HPLC (acetonitrile/water)

Sources & evidence

ORD record
ord-54b8f0c502f146648ec4f13087793a37
Source dataset
uspto-grants-2014_07
Patent number
US08772498B2

Reaction notes

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