Ethyl Acetate → 5-[3-(5-Fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-ylmethoxy]-pyrazine-2-carboxylic acid (tetrahydro-pyran-4-yl)-amide

HRID 600488Notes

Reaction equation

HRID 600488 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]([CH2:13][O:14][C:15]3[N:16]=[CH:17][C:18]([C:21]([OH:23])=O)=[N:19][CH:20]=3)=[C:11]([CH3:24])[O:10][N:9]=2)=[N:6][CH:7]=1.CC1O[N:29]=[C:28](C2C=CC=CC=2)[C:27]=1[CH2:37][O:38][C:39]1N=CC(C(O)=O)=N[CH:44]=1.NC1CCOCC1.C(OCC)(=O)C>CO.C(Cl)Cl>[O:38]1[CH2:37][CH2:27][CH:28]([NH:29][C:21]([C:18]2[CH:17]=[N:16][C:15]([O:14][CH2:13][C:12]3[C:8]([C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:7][N:6]=4)=[N:9][O:10][C:11]=3[CH3:24])=[CH:20][N:19]=2)=[O:23])[CH2:44][CH2:39]1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 4192234-AminotetrahydropyranHCID 68443500HCID 68443500, compoundHCID 684440545-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyrazine-2-carboxylic acid

Product 1

HCID 469378455-[3-(5-Fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-ylmethoxy]-pyrazine-2-carboxylic acid (tetrahydro-pyran-4-yl)-amide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

As described for example 2b, 5-[3-(5-fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-ylmethoxy]-pyrazine-2-carboxylic acid (44 mg, 13.3 mmol), instead of 5-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyrazine-2-carboxylic acid, was converted, using 4-aminotetrahydropyran instead of aminomethylcyclopropane, to the title compound (SiO2, ethyl acetate then DCM:MeOH=90:10, 31 mg, 56%) which was obtained as a white solid. MS: m/e=414.2 [M+H]+.

Sources & evidence

ORD record
ord-567c9c8a7adc4e578e6af11ad124c807
Source dataset
uspto-grants-2011_03
Patent number
US07902201B2

Reaction notes

Loading…