4-Aminotetrahydropyran → HCID 49804753, compound

HRID 1807490Notes

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

Participants

Reactant 2

HCID 4192234-Aminotetrahydropyran

HCID 66643579HCID 66643579, compound

Product 1

HCID 49804753HCID 49804753, compoundYield 19%

Procedure

As described for example 1e, 6-(5-methyl-3-propyl-isoxazol-4-ylmethoxy)-nicotinic acid methyl ester (145 mg, 0.50 mmol) was converted, using 4-aminotetrahydropyran instead of isopropylamine, to the title compound (35 mg, 19%) which was obtained as a white solid after purification by chromatography (silica, 0-6% methanol in dichloromethane) and after trituration with diisopropyl ether. MS: m/e=360.3 [M+H]+.

Sources & evidence

ORD record: ord-ae5e3e32c4434581a2330473fcf6bc1b
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08357703B2

Reaction notes

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