1,3-Propanediol → 2-({[2-(4-Chlorophenyl)-1,3-thiazol-4-yl]methyl}sulphanyl)-6-(3-hydroxypropoxy)-4-phenylpyridine-3,5-dicarbonitrile

HRID 1630721Notes

Reaction equation

HRID 1630721 reaction equation
[CH2:1]([OH:5])[CH2:2][CH2:3][OH:4].CC(C)([O-])C.[K+].Cl[C:13]1[C:18]([C:19]#[N:20])=[C:17]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:16]([C:27]#[N:28])=[C:15]([S:29][CH2:30][C:31]2[N:32]=[C:33]([C:36]3[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][CH:37]=3)[S:34][CH:35]=2)[N:14]=1>CN(C=O)C>[Cl:42][C:39]1[CH:40]=[CH:41][C:36]([C:33]2[S:34][CH:35]=[C:31]([CH2:30][S:29][C:15]3[C:16]([C:27]#[N:28])=[C:17]([C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)[C:18]([C:19]#[N:20])=[C:13]([O:4][CH2:3][CH2:2][CH2:1][OH:5])[N:14]=3)[N:32]=2)=[CH:37][CH:38]=1

Participants

5

Reactant 3

HCID 104421,3-PropanediolHCID 23665647Potassium tert-butoxideHCID 866542112-Chloro-6-({[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl}sulphanyl)-4-phenylpyridine-3,5-dicarbonitrile

Product 1

HCID 672163272-({[2-(4-Chlorophenyl)-1,3-thiazol-4-yl]methyl}sulphanyl)-6-(3-hydroxypropoxy)-4-phenylpyridine-3,5-dicarbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

68 μl (0.939 mmol) of 1,3-propanediol are initially charged in 2 ml of DMF, 38 mg (0.344 mmol) of potassium tert-butoxide are added and the mixture is stirred for 15 minutes, after which 150 mg (0.313 mmol) of 2-chloro-6-({[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl}sulphanyl)-4-phenylpyridine-3,5-dicarbonitrile, dissolved in 2 ml of DMF, are added. The reaction mixture is stirred at room temperature for 1 hour and then purified by preparative HPLC (acetonitrile/water: 10:90→95:5, with 0.1% TFA added). This gives 98 mg (59% of theory) of the target compound.

Workup

  1. additionare added
  2. stirringThe reaction mixture is stirred at room temperature for 1 hour
  3. custompurified by preparative HPLC (acetonitrile/water: 10:90→95:5, with 0.1% TFA added)

Sources & evidence

ORD record
ord-a19a44a000304e289eb611c8e873636e
Source dataset
uspto-grants-2014_07
Patent number
US08791146B2

Reaction notes

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