Diisopropylamine → HCID 178456730, compound

HRID 641091Notes

Reaction equation

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

Participants

Reactant 2

HCID 7912Diisopropylamine

HCID 178505700HCID 178505700, compound

Product 2

HCID 178456730HCID 178456730, compound

HCID 178456843HCID 178456843, compound

Procedure

In a stainless steel autoclave, 700 mg (2.0 mmol) of 3-(2-chloro-6-fluorophenyl)-2,4-dichloro-6-([1,2,4]triazolyl)pyridine (Example A) and 15 g of diisopropylamine were heated at 160° C. for 12 h. The volatile components were removed under reduced pressure and the residue was chromatographed on silica gel using cyclohexane/ethyl acetate. It was possible to isolate 240 mg of 2-chloro-3-(2-chloro-6-fluorophenyl)-4-(2-propylamino)-6-([1,2,4]triazolyl)pyridine (m.p. 152° C.) and 310 mg of 4-chloro-3-(2-chloro-6-fluorophenyl)-2-(2-propylamino)-6-([1,2,4]triazolyl)pyridine (m.p. 152° C.).

Workup

customThe volatile components were removed under reduced pressure
customthe residue was chromatographed on silica gel

Sources & evidence

ORD record: ord-499de7d5b69f4cf5a76fff9384e00eea
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07695728B2

Reaction notes

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