4-Aminotetrahydropyran → HCID 24783155, compound

HRID 1984665Notes

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[C:13]#[C:14][C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][N:23]=1)[C:18]([OH:20])=O.[NH2:24][CH:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1>>[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:3]=1[C:13]#[C:14][C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][N:23]=1)[C:18]([NH:24][CH:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1)=[O:20]

Participants

Reactant 2

HCID 4192234-Aminotetrahydropyran

HCID 68852366HCID 68852366, compound

Product 1

HCID 24783155HCID 24783155, compoundYield 73%

Procedure

As described for example 7b, 2-(5-methyl-3-phenyl-isoxazol-4-ylethynyl)-isonicotinic acid (50 mg; 0.16 mmol) instead of 3-(5-methyl-3-phenyl-isoxazol-4-ylethynyl)-benzoic acid was converted (using 4-amino-tetrahydropyrane instead of aminomethylcyclopropane) to the title compound (SiO2, heptane:ethyl acetate=95:5 to 0:100, 46 mg, 73%) which was obtained as a yellow solid. MS: m/e=388.2 [M+H]+.

Sources & evidence

ORD record: ord-ac97d16060404e869ab6469495a123a8
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07544704B2

Reaction notes

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