Ethanolamine → HCID 58504053, compound

HRID 2407811Notes

Reaction equation

HRID 2407811 reaction equation
[NH2:1][C:2]1[C:7]([Cl:8])=[C:6](Cl)[N:5]=[C:4]([C:10]([NH:12][CH2:13][CH:14]2[CH2:19][CH2:18][N:17]([CH2:20][C:21]3[S:25][C:24]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=4)=[N:23][CH:22]=3)[CH2:16][CH2:15]2)=[O:11])[CH:3]=1.[NH2:32][CH2:33][CH2:34][OH:35]>CC(N(C)C)=O>[NH2:1][C:2]1[C:7]([Cl:8])=[C:6]([NH:32][CH2:33][CH2:34][OH:35])[N:5]=[C:4]([C:10]([NH:12][CH2:13][CH:14]2[CH2:19][CH2:18][N:17]([CH2:20][C:21]3[S:25][C:24]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=4)=[N:23][CH:22]=3)[CH2:16][CH2:15]2)=[O:11])[CH:3]=1

Participants

4

Reactant 2

HCID 700EthanolamineHCID 585039374-amino-5,6-dichloro-N-((1-((2-(pyridin-2-yl)thiazol-5-yl)methyl)piperidin-4-yl)methyl)picolinamide

Product 1

HCID 58504053HCID 58504053, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
160 °C

Procedure

The compound prepared in Example 407 (0.065 g) and 2-aminoethanol (0.008 g) were suspended in dimethyl acetamide (3 mL) and heated at 160° C. for 30 minutes. The reaction mixture was heated at 200° C. for 1 hour. The reaction mixture was cooled to room temperature and partitioned between saturated aqueous sodium bicarbonate and ethyl acetate. The organics were washed with brine, dried, magnesium sulfate and concentrated under reduced pressure to afford the crude material. The crude material was purified by flash column chromatography (eluant: 1-4% (9:1=methanol:ammonium hydroxide)/ethyl acetate) to furnish the title compound (0.037 g), possessing the following physical data.

Workup

  1. temperatureThe reaction mixture was heated at 200° C. for 1 hour
  2. temperatureThe reaction mixture was cooled to room temperature
  3. custompartitioned between saturated aqueous sodium bicarbonate and ethyl acetate
  4. washThe organics were washed with brine
  5. customdried
  6. concentrationmagnesium sulfate and concentrated under reduced pressure
  7. customto afford the crude material
  8. customThe crude material was purified by flash column chromatography (eluant: 1-4% (9:1=methanol:ammonium hydroxide)/ethyl acetate)

Sources & evidence

ORD record
ord-d63403cb37624e05853f07bbfe8c589e
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

Loading…