Ethanolamine → 4-Amino-3-{5-[5-(4-chloro-benzyl)-[1,3,4]oxadiazol-2-yl]-2-methyl-phenoxymethyl}-thieno[3,2-c]pyridine-7-carboxylic acid (2-hydroxy-ethyl)-amide

HRID 2081101Notes

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[O:25][C:26]([CH2:29][C:30]5[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=5)=[N:27][N:28]=4)[CH:21]=[CH:20][C:19]=3[CH3:37])[C:8]=2[C:9]([NH2:12])=[N:10][CH:11]=1)=[O:5])C.[CH2:38]([CH2:40][NH2:41])[OH:39]>CS(C)=O>[OH:39][CH2:38][CH2:40][NH:41][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[O:25][C:26]([CH2:29][C:30]5[CH:31]=[CH:32][C:33]([Cl:36])=[CH:34][CH:35]=5)=[N:27][N:28]=4)[CH:21]=[CH:20][C:19]=3[CH3:37])[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-{5-[5-(4-chloro-benzyl)-[1,3,4]oxadiazol-2-yl]-2-methyl-phenoxymethyl}-thieno[3,2-c]pyridine-7-carboxylic acid ethyl ester (0.07 g, 0.13 mmol) (from Example 42 supra) in dimethylsulfoxide (0.5 mL) was treated with ethanolamine (1.5 mL) and heated at 160° C. for 2.8 hours in a microwave reactor. The reaction mixture was purified by C18 column chromatography and SFC column chromatography to give 4-amino-3-{5-[5-(4-chloro-benzyl)-[1,3,4]oxadiazol-2-yl]-2-methyl-phenoxymethyl}-thieno[3,2-c]pyridine-7-carboxylic acid (2-hydroxy-ethyl)-amide as a white powder. (Yield 8 mg, 11%).

Workup

customThe reaction mixture was purified by C18 column chromatography and SFC column chromatography

Sources & evidence

ORD record: ord-364c5131e09c44588f0b0d440e4c0b4b
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07932390B2

Reaction notes

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