4-Aminotetrahydropyran → HCID 49801026, compound

HRID 1807516Notes

Reaction equation

CO[C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[C:13]([CH2:17][CH2:18][CH2:19][CH3:20])=[N:14][O:15][CH:16]=2)=[N:6][CH:5]=1.[NH2:22][CH:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1>>[CH2:17]([C:13]1[C:12]([CH2:11][O:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([NH:22][CH:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)=[O:21])=[CH:5][N:6]=2)=[CH:16][O:15][N:14]=1)[CH2:18][CH2:19][CH3:20]

Participants

Reactant 2

HCID 4192234-Aminotetrahydropyran

HCID 66643605HCID 66643605, compound

Product 1

HCID 49801026HCID 49801026, compoundYield 73%

Procedure

As described for example 25e, 6-(3-butyl-isoxazol-4-ylmethoxy)-nicotinic acid methyl ester (200 mg, 0.69 mmol) was converted, using 4-aminotetrahydropyran instead of isopropylamine, to the title compound (180 mg, 73%) which was obtained as a white solid after purification by chromatography (silica, 40 to 60% ethyl acetate in heptane). MS: m/e=360.2 [M+H]+.

Sources & evidence

ORD record: ord-05c26fd27ea8465a82029f835a0c0de7
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08357703B2

Reaction notes

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