4-Aminotetrahydropyran → HCID 68851528, compound

HRID 1984646Notes

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:23]=[CH:22][C:18]([C:19](O)=[O:20])=[CH:17][CH:16]=1.[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:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[C:13]#[C:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([NH:24][CH:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)=[O:20])=[CH:17][CH:16]=1

Participants

Reactant 2

HCID 4192234-Aminotetrahydropyran

HCID 68852658HCID 68852658, compound

Product 1

HCID 68851528HCID 68851528, compoundYield 88%

Procedure

As described for example 7b, 4-(5-methyl-3-phenyl-isoxazol-4-ylethynyl)-benzoic acid (250 mg; 0.82 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, 281 mg, 88%) which was obtained as a white solid. MS: m/e=387.1 [M+H]+.

Sources & evidence

ORD record: ord-3176fe333d0b4a849abe02d148c6cb58
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07544704B2

Reaction notes

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