Propylene Oxide → HCID 66897662, compound

HRID 1969487Notes

Reaction equation

HRID 1969487 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:14]=[CH:13][NH:12][N:11]=2)[C:5]([C:15]#[N:16])=[C:4]([S:17][CH2:18][C:19]2[N:20]=[C:21]([C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=3)[S:22][CH:23]=2)[N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:37][CH:38]1[CH2:40][O:39]1>>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:14]=[CH:13][N:12]([CH2:37][CH:38]([OH:39])[CH3:40])[N:11]=2)[C:5]([C:15]#[N:16])=[C:4]([S:17][CH2:18][C:19]2[N:20]=[C:21]([C:24]3[CH:25]=[CH:26][C:27]([Cl:30])=[CH:28][CH:29]=3)[S:22][CH:23]=2)[N:3]=1

Participants

4

Reactant 3

HCID 6378Propylene OxideHCID 10796Cesium carbonateHCID 178510466HCID 178510466, compound

Product 1

HCID 66897662HCID 66897662, compound

Procedure

10 mg (0.022 mmol) of 2-amino-6-({[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl}sulfanyl)-4-(1H-pyrazol-3-yl)pyridine-3,5-dicarbonitrile were dissolved in 1 ml of 2-methyloxirane, and a spatula tip of cesium carbonate was added. The reaction mixture was stirred at room temperature overnight, concentrated, taken up in a little methanol and purified by preparative HPLC (acetonitrile/water: 10:90→95:5, 0.1% TFA added). This gave 10 mg (86% of theory) of the target compound.

Workup

  1. concentrationconcentrated
  2. custompurified by preparative HPLC (acetonitrile/water: 10:90→95:5, 0.1% TFA added)

Sources & evidence

ORD record
ord-dfcdaae46db141daa03a4cd7b7cdf1a1
Source dataset
uspto-grants-2013_04
Patent number
US08426602B2

Reaction notes

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