Ethanolamine → HCID 86606219, compound

HRID 908178Notes

Reaction equation

HRID 908178 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH:17][C:18]2[CH:23]=[N:22][CH:21]=[CH:20][N:19]=2)[S:5][C:6]=1[C:7]1[CH:8]=[C:9]([S:13](Cl)(=[O:15])=[O:14])[CH:10]=[CH:11][CH:12]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH2:30]([CH2:32][NH2:33])[OH:31]>O1CCOCC1>[OH:31][CH2:30][CH2:32][NH:33][S:13]([C:9]1[CH:10]=[CH:11][CH:12]=[C:7]([C:6]2[S:5][C:4]([NH:17][C:18]3[CH:23]=[N:22][CH:21]=[CH:20][N:19]=3)=[N:3][C:2]=2[CH3:1])[CH:8]=1)(=[O:15])=[O:14]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 10340Sodium CarbonateHCID 85996838HCID 85996838, compound

Product 1

HCID 86606219HCID 86606219, compoundYield 14.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-[4-Methyl-2-(pyrazin-2-ylamino)-thiazol-5-yl]-benzenesulfonyl chloride (42c) (0.251 g, 0.68 mmol) is dissolved in dioxane (10 ml). The solution is treated with 2M aqueous sodium carbonate (0.7 ml, 1.36 mmol) followed by the addition of ethanolamine (0.125 ml, 2.05 mmol). The reaction mixture is stirred overnight. The solvent is removed in vacuo and the residue is taken into water (10 ml)/ethylacetate (30 ml) and sonicated. The layers are separated then the aqueous layer is extracted with ethyl acetate (2×30 ml). The combined organic layers are dried over MgSO4, filtered and concentrated to give a residue which is purified by prep LC-MS to give the titled compound (0.038 g, 14%)

Workup

  1. customThe solvent is removed in vacuo
  2. customsonicated
  3. customThe layers are separated
  4. extractionthe aqueous layer is extracted with ethyl acetate (2×30 ml)
  5. dry with materialThe combined organic layers are dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a residue which
  9. customis purified by prep LC-MS

Sources & evidence

ORD record
ord-d9a47afd3273431f81f1b8de318b6b9d
Source dataset
uspto-grants-2011_09
Patent number
US08017608B2

Reaction notes

Loading…