2-Amino-2-methyl-1-propanol → 2-{(E)-2-[3-(5-Fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-yl]-vinyl}-4-methyl-thiazole-5-carboxylic acid (2-hydroxy-1,1-dimethyl-ethyl)-amide

HRID 1923578Notes

Reaction equation

HRID 1923578 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12](/[CH:13]=[CH:14]/[C:15]3[S:16][C:17]([C:21]([OH:23])=O)=[C:18]([CH3:20])[N:19]=3)=[C:11]([CH3:24])[O:10][N:9]=2)=[N:6][CH:7]=1.[NH2:25][C:26]([CH3:30])([CH3:29])[CH2:27][OH:28]>CO.O>[OH:28][CH2:27][C:26]([NH:25][C:21]([C:17]1[S:16][C:15](/[CH:14]=[CH:13]/[C:12]2[C:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][N:6]=3)=[N:9][O:10][C:11]=2[CH3:24])=[N:19][C:18]=1[CH3:20])=[O:23])([CH3:30])[CH3:29]

Participants

4

Reactant 2

HCID 118072-Amino-2-methyl-1-propanolHCID 666436302-{(E)-2-[3-(5-Fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-yl]-vinyl}-4-methyl-thiazole-5-carboxylic acid

Product 1

HCID 595685062-{(E)-2-[3-(5-Fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-yl]-vinyl}-4-methyl-thiazole-5-carboxylic acid (2-hydroxy-1,1-dimethyl-ethyl)-amideYield 30%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

As described for example 71d, 2-{(E)-2-[3-(5-fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-yl]-vinyl}-4-methyl-thiazole-5-carboxylic acid (69 mg, 0.2 mmol) was converted, using 2-amino-2-methyl-1-propanol instead of isopropylamine, to the title compound (25 mg, 30%) which was obtained as a white solid after trituration from methanol/water. MS: m/e=417.2 [M+H]+.

Sources & evidence

ORD record
ord-efa79035fe034562b8bd6b9d3867b7f1
Source dataset
uspto-grants-2012_05
Patent number
US08178522B2

Reaction notes

Loading…