1,3-Propanediol → HCID 44548709, compound

HRID 1500115Notes

Reaction equation

HRID 1500115 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[S:25][CH:24]=[N:23][CH:22]=2)[C:16]([C:26]#[N:27])=[C:15]([S:28][CH2:29][C:30]2[N:31]=[C:32]([C:35]3[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=3)[S:33][CH:34]=2)[N:14]=1>CN(C=O)C>[Cl:41][C:38]1[CH:39]=[CH:40][C:35]([C:32]2[S:33][CH:34]=[C:30]([CH2:29][S:28][C:15]3[C:16]([C:26]#[N:27])=[C:17]([C:21]4[S:25][CH:24]=[N:23][CH:22]=4)[C:18]([C:19]#[N:20])=[C:13]([O:4][CH2:3][CH2:2][CH2:1][OH:5])[N:14]=3)[N:31]=2)=[CH:36][CH:37]=1

Participants

5

Reactant 3

HCID 104421,3-PropanediolHCID 23665647Potassium tert-butoxideHCID 866542122-Chloro-6-({[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl}sulfanyl)-4-(1,3-thiazol-5-yl)pyridine-3,5-dicarbonitrile

Product 1

HCID 44548709HCID 44548709, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

30 μl (0.419 mmol) of 1,3-propanediol are initially charged in 2 ml of DMF, 18 mg (0.154 mmol) of potassium tert-butoxide are added and the mixture is stirred for 15 minutes, after which 75 mg (0.14 mmol) of 2-chloro-6-({[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl}sulphanyl)-4-(1,3-thiazol-5-yl)pyridine-3,5-dicarbonitrile, dissolved in 2 ml of DMF, are added. The reaction mixture is stirred at room temperature for 30 minutes and then purified by preparative HPLC (acetonitrile/water: 10:90→95:5). This gives 11 mg (15% of theory) of the target compound.

Workup

  1. additionare added
  2. stirringThe reaction mixture is stirred at room temperature for 30 minutes
  3. custompurified by preparative HPLC (acetonitrile/water: 10:90→95:5)

Sources & evidence

ORD record
ord-e1ae5333a24546a997288ef1c9ff9ec6
Source dataset
uspto-grants-2015_12
Patent number
US09205077B2

Reaction notes

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