Trimethyl orthoformate → HCID 86761743, compound

HRID 1805263Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[C:13]([C:14]([NH:16][NH2:17])=[O:15])=[C:12]([C:18]2[CH:19]=[N:20][N:21]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[F:33])[C:22]=2[C:23]([F:26])([F:25])[F:24])[O:11][N:10]=1.[CH:34](OC)(OC)OC>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[C:13]([C:14]2[O:15][CH:34]=[N:17][N:16]=2)=[C:12]([C:18]2[CH:19]=[N:20][N:21]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[F:33])[C:22]=2[C:23]([F:25])([F:26])[F:24])[O:11][N:10]=1

Participants

Reactant 2

HCID 9005Trimethyl orthoformate

HCID 86668520HCID 86668520, compound

Product 1

HCID 86761743HCID 86761743, compoundYield 46.4%

Procedure

A solution of 3-(2-chloro-6-fluorophenyl)-5-(1-(2-fluorophenyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)isoxazole-4-carbohydrazide (0.076 g, 0.157 mmol) in 4 g trimethyl orthoformate was kept in a sealed tube at 125° C. for 3 days. The solution was evaporated to dryness and the residue was crystallized from heptane to give 36 mg (46%) of a yellowish solid of example 15. Result of LC/MS MH+: 493.75; 1H NMR (methanol-d4; 400 MHz) δ ppm: 7.30-7.35 (1H, m, CH-arom.), 7.42-7.48 (3H, m, CH-arom.), 7.60-7.70 (3H, m, CH-arom.), 8.51 (1H, s, CH-oxadiazole), 8.93 (1H, s, CH-pyraz.)

Workup

customThe solution was evaporated to dryness
customthe residue was crystallized from heptane

Sources & evidence

ORD record: ord-b748ebff07bc4b81bad8cf1615a00466
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354436B2

Reaction notes

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