4-Aminotetrahydropyran → 4-Methyl-6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazine-3-carboxylic acid (tetrahydro-pyran-4-yl)-amide

HRID 548843Notes

Reaction equation

HRID 548843 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[C:11]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:12][O:13][C:14]=2[CH3:15])[N:5]=[N:4][C:3]=1[C:22]([OH:24])=O.CC1O[N:29]=[C:28](C2C=CC=CC=2)[C:27]=1[CH2:37][O:38][C:39]1N=NC(C(O)=O)=C[CH:40]=1.NC1CCOCC1>>[O:38]1[CH2:37][CH2:27][CH:28]([NH:29][C:22]([C:3]2[N:4]=[N:5][C:6]([O:8][CH2:9][C:10]3[C:11]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)=[N:12][O:13][C:14]=3[CH3:15])=[CH:7][C:2]=2[CH3:1])=[O:24])[CH2:40][CH2:39]1

Participants

4

Reactant 3

HCID 4192234-AminotetrahydropyranHCID 665989756-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazine-3-carboxylic acidHCID 671581534-Methyl-6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazine-3-carboxylic acid

Product 1

HCID 426296524-Methyl-6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazine-3-carboxylic acid (tetrahydro-pyran-4-yl)-amideYield 62%

Procedure

As described for example 11b, 4-methyl-6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazine-3-carboxylic acid (200 mg, 0.61 mmol), instead of 6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazine-3-carboxylic acid, was converted, using 4-amino-tetrahydropyran instead of thiomorpholine 1,1-dioxide, to the title compound (SiO2, heptane:ethyl acetate=100:0 to 60:40, 156 mg, 62%) which was obtained as a white solid. MS: m/e=409.3 [M+H]−.

Sources & evidence

ORD record
ord-a53ae8f1fc20486fb438fd36e765d249
Source dataset
uspto-grants-2011_05
Patent number
US07943619B2

Reaction notes

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