Ethanolamine → HCID 178433946, compound

HRID 2081117Notes

Reaction equation

HRID 2081117 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].C([O:7][C:8]([C:10]1[C:11]2[S:19][CH:18]=[C:17]([CH2:20][O:21][C:22]3[CH:27]=[C:26]([C:28]4[NH:32][C:31]([CH3:33])=[N:30][N:29]=4)[CH:25]=[CH:24][C:23]=3[CH3:34])[C:12]=2[C:13]([NH2:16])=[N:14][CH:15]=1)=O)C>CS(C)=O>[OH:2][CH2:1][CH2:3][NH:4][C:8]([C:10]1[C:11]2[S:19][CH:18]=[C:17]([CH2:20][O:21][C:22]3[CH:27]=[C:26]([C:28]4[NH:32][C:31]([CH3:33])=[N:30][N:29]=4)[CH:25]=[CH:24][C:23]=3[CH3:34])[C:12]=2[C:13]([NH2:16])=[N:14][CH:15]=1)=[O:7]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 178469826HCID 178469826, compound

Product 1

HCID 178433946HCID 178433946, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
135 °C

Procedure

Ethanolamine (1.5 mL; 24.9 mmol) (Aldrich) was added to a suspension of 4-amino-3-[2-methyl-5-(5-methyl-4H-[1,2,4]triazol-3-yl)-phenoxymethyl]-thieno[3,2-c]pyridine-7-carboxylic acid ethyl ester (68.4 mg; 0.162 mmol) (from Example 62 supra) in dimethylsulfoxide (0.5 mL). The mixture was heated in a microwave reactor at 135° C. for 90 minutes and then for 1 hour at 140° C. The crude reaction mixture was concentrated under high vacuum with heat to remove most of the ethanolamine and DMSO. The residue was diluted with water, causing a milky precipitate to drop out of solution. The solid was collected by filtration, washed with water and dried. The material was then triturated with hot methanol to give 4-amino-3-[2-methyl-5-(5-methyl-4H-[1,2,4]triazol-3-yl)-phenoxymethyl]-thieno[3,2-c]pyridine-7-carboxylic acid (2-hydroxy-ethyl)-amide as an off-white solid. (Yield 48 mg, 67.8%).

Workup

  1. customThe crude reaction mixture
  2. concentrationwas concentrated under high vacuum
  3. temperaturewith heat
  4. customto remove most of the ethanolamine and DMSO
  5. additionThe residue was diluted with water
  6. filtrationThe solid was collected by filtration
  7. washwashed with water
  8. customdried
  9. customThe material was then triturated with hot methanol

Sources & evidence

ORD record
ord-75e0967c2de34a768dce37af8d270476
Source dataset
uspto-grants-2011_04
Patent number
US07932390B2

Reaction notes

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