Ethanolamine → 3-[5-(3-Chloro-benzoylamino)-2-methyl-phenoxymethyl]-thieno[3,2-c]pyridine-7-carboxylic acid (2-hydroxy-ethyl)-amide

HRID 1671524Notes

Reaction equation

HRID 1671524 reaction equation
C(O[C:4]([C:6]1[C:7]2[S:14][CH:13]=[C:12]([CH2:15][O:16][C:17]3[CH:22]=[C:21]([NH:23][C:24](=[O:32])[C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[CH:26]=4)[CH:20]=[CH:19][C:18]=3[CH3:33])[C:8]=2[CH:9]=[N:10][CH:11]=1)=[O:5])C.[CH2:34]([CH2:36][NH2:37])[OH:35]>CS(C)=O>[OH:35][CH2:34][CH2:36][NH:37][C:4]([C:6]1[C:7]2[S:14][CH:13]=[C:12]([CH2:15][O:16][C:17]3[CH:22]=[C:21]([NH:23][C:24](=[O:32])[C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[CH:26]=4)[CH:20]=[CH:19][C:18]=3[CH3:33])[C:8]=2[CH:9]=[N:10][CH:11]=1)=[O:5]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 248006193-[5-(3-Chloro-benzoylamino)-2-methyl-phenoxymethyl]-thieno[3,2-c]pyridine-7-carboxylic acid ethyl ester

Product 1

HCID 248006203-[5-(3-Chloro-benzoylamino)-2-methyl-phenoxymethyl]-thieno[3,2-c]pyridine-7-carboxylic acid (2-hydroxy-ethyl)-amide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of 3-[5-(3-chloro-benzoylamino)-2-methyl-phenoxymethyl]-thieno[3,2-c]pyridine-7-carboxylic acid ethyl ester (315 mg, 0.65 mmol) (from Example 24 supra) in methyl sulfoxide (3 mL) and ethanolamine (9 mL) (Aldrich) was heated at 135° C. for 2 hours in a microwave reactor. After cooling to room temperature, the precipitate was filtered off, washed thoroughly with MeOH and dried to give 3-[5-(3-chloro-benzoylamino)-2-methyl-phenoxymethyl]-thieno[3,2-c]pyridine-7-carboxylic acid (2-hydroxy-ethyl)-amide as a white solid. (Yield 267 mg, 82.8%).

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe precipitate was filtered off
  3. washwashed thoroughly with MeOH
  4. customdried

Sources & evidence

ORD record
ord-dae7a6f0fb7449318f0304a4011a539d
Source dataset
uspto-grants-2011_08
Patent number
US07994321B2

Reaction notes

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