6-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-nicotinic acid → (6,7-Dihydro-5H-pyrazolo[1,5-a]pyrimidin-4-yl)-[6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridin-3-yl]-methanone

HRID 1521043Notes

Reaction equation

HRID 1521043 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[CH2:13][O:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][N:16]=1.Cl.[N:25]1[N:29]2[CH2:30][CH2:31][CH2:32][NH:33][C:28]2=[CH:27][CH:26]=1>>[N:25]1[N:29]2[CH2:30][CH2:31][CH2:32][N:33]([C:19]([C:18]3[CH:17]=[N:16][C:15]([O:14][CH2:13][C:3]4[C:4]([C:7]5[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=5)=[N:5][O:6][C:2]=4[CH3:1])=[CH:23][CH:22]=3)=[O:21])[C:28]2=[CH:27][CH:26]=1

Participants

3

Reactant 2

HCID 665992136-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-nicotinic acidHCID 136275138HCID 136275138, compound

Product 1

HCID 68458124(6,7-Dihydro-5H-pyrazolo[1,5-a]pyrimidin-4-yl)-[6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridin-3-yl]-methanoneYield 31%

Procedure

As described for example 8b, 6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-nicotinic acid (100 mg, 0.32 mmol) was converted, using 4,5,6,7-tetrahydropyrazolo(1,5-a)-pyrimidine hydrochloride instead of methylamine, to the title compound (41 mg, 31%) which was obtained as a light yellow solid after crystallisation from ethyl acetate:hexane. MS: m/e=416.4 [M+H]′.

Sources & evidence

ORD record
ord-c5feebaac2d14e0f924d34e6d56318e4
Source dataset
uspto-grants-2015_07
Patent number
US09073908B2

Reaction notes

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