Oxalic acid--2-oxa-6-azaspiro(3.3)heptane (1/1) → [6-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridin-3-yl]-(2-oxa-6-aza-spiro[3.3]hept-6-yl)-methanone

HRID 331787Notes

Reaction equation

HRID 331787 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[CH2:13][O:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][N:16]=1.C(O)(=O)C(O)=O.[CH2:30]1[C:33]2([CH2:36][NH:35][CH2:34]2)[CH2:32][O:31]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[CH2:13][O:14][C:15]1[N:16]=[CH:17][C:18]([C:19]([N:35]2[CH2:36][C:33]3([CH2:30][O:31][CH2:32]3)[CH2:34]2)=[O:21])=[CH:22][CH:23]=1

Participants

3

Reactant 2

HCID 53308464Oxalic acid--2-oxa-6-azaspiro(3.3)heptane (1/1)HCID 665992136-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-nicotinic acid

Product 1

HCID 57336136[6-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridin-3-yl]-(2-oxa-6-aza-spiro[3.3]hept-6-yl)-methanoneYield 76%

Procedure

As described for example 8b, 6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-nicotinic acid (100 mg, 0.32 mmol) was converted, using 2-oxa-6-aza-spiro[3.3]heptane oxalate instead of methylamine, to the title compound (96 mg, 76%) which was obtained as an off white solid. MS: m/e=392.4 [M+H]+.

Sources & evidence

ORD record
ord-301944ceef864197bb4bd7919413232d
Source dataset
uspto-grants-2014_11
Patent number
US08877782B2

Reaction notes

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