Ethanolamine → 4-amino-3-[2-methyl-5-(1-methyl-1H-[1,2,3]triazol-4-yl)-phenoxymethyl]-thieno[3,2-c]pyridine-7-carboxylic acid (2-hydroxy-ethyl)-amide

HRID 2081082Notes

Reaction equation

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

Participants

Conditions

Temperature: 160 °C

Procedure

A solution of 4-amino-3-[2-methyl-5-(1-methyl-1H-[1,2,3]triazol-4-yl)-phenoxymethyl]-thieno[3,2-c]pyridine-7-carboxylic acid ethyl ester (0.050 g, 0.11 mmol) (from Example 23 supra) in dimethylsulfoxide (0.5 mL) was treated with ethanolamine (1.5 mL) (Aldrich) and heated at 160° C. for 2 hours in a microwave reactor. The reaction mixture was purified by C18 column eluting with acetonitrile-water to give 4-amino-3-[2-methyl-5-(1-methyl-1H-[1,2,3]triazol-4-yl)-phenoxymethyl]-thieno[3,2-c]pyridine-7-carboxylic acid (2-hydroxy-ethyl)-amide as a white powder. (Yield 31.0 mg, 60%).

Workup

customThe reaction mixture was purified by C18 column
washeluting with acetonitrile-water

Sources & evidence

ORD record: ord-ab94cb155bec4ce9812ab9460baa11d2
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07932390B2

Reaction notes

Loading…