Sec-Butylamine → HCID 59007730, compound

HRID 641092Notes

Reaction equation

HRID 641092 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:22])=[N:11][C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)=[CH:13][C:14]=1[Cl:15].[CH3:23][CH:24]([NH2:27])[CH2:25][CH3:26]>>[Cl:15][C:14]1[CH:13]=[C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[N:11]=[C:10]([NH:27][CH:24]([CH2:25][CH3:26])[CH3:23])[C:9]=1[C:3]1[C:4]([F:8])=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1].[Cl:22][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:27][CH:24]([CH2:25][CH3:26])[CH3:23])[CH:13]=[C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[N:11]=1

Participants

4

Reactant 2

HCID 24874Sec-ButylamineHCID 59007746HCID 59007746, compound

Product 2

HCID 59007730HCID 59007730, compoundHCID 59007731HCID 59007731, compound

Procedure

In a stainless steel autoclave, 2.0 g (5.7 mmol) of 3-(2-chloro-6-fluorophenyl)-2,4-dichloro-6-(pyridin-2-yl)pyridine (Example B) and 15 g of racemic 2-butylamine were heated at 180° 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 450 mg of 4-chloro-3-(2-chloro-6-fluorophenyl)-2-(2-butylamino)-6-(pyridin-2-yl)pyridine (1H-NMR (CDCl3) δ=0.90 (m); 1.20 (m); 1.55 (m); 3.80 (broad); 4.27 (m); 7.15-7.45 (m); 7.80 (t); 7.90 (s); 8.42 (d); 8.67 (m)) and 370 mg of 2-chloro-3-(2-chloro-6-fluorophenyl)-4-(2-butylamino)-6-(pyridin-2-yl)pyridine (1H-NMR (CDCl3) δ=0.90 (m); 1.20 (m); 1.50 (m); 3.67 (broad); 3.77 (m); 7.15-7.45 (m); 7.75 (s); 7.82 (t); 8.42 (d); 8.67 (m)). The compounds are present as rotamer mixtures.

Workup

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

Sources & evidence

ORD record
ord-ac600136bc54478ba6b2656414bc1c68
Source dataset
uspto-grants-2010_04
Patent number
US07695728B2

Reaction notes

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