[4-(2-Chloro-4-dimethylamino-5-fluoro-phenyl)-3-nitro-pyridin-2-yl]-(1-cyclopropyl-propyl)-amine → 4-(2-chloro-4-dimethylamino-5-fluoro-phenyl)-N2-(1-cyclopropyl-propyl)-pyridine-2,3-diamine

HRID 1831585Notes

Reaction equation

HRID 1831585 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N:8]([CH3:10])[CH3:9])[C:5]([F:11])=[CH:4][C:3]=1[C:12]1[CH:17]=[CH:16][N:15]=[C:14]([NH:18][CH:19]([CH:22]2[CH2:24][CH2:23]2)[CH2:20][CH3:21])[C:13]=1[N+:25]([O-])=O.Cl[Sn]Cl.O>>[Cl:1][C:2]1[CH:7]=[C:6]([N:8]([CH3:9])[CH3:10])[C:5]([F:11])=[CH:4][C:3]=1[C:12]1[CH:17]=[CH:16][N:15]=[C:14]([NH:18][CH:19]([CH:22]2[CH2:23][CH2:24]2)[CH2:20][CH3:21])[C:13]=1[NH2:25]

Participants

3

Reactant 2

HCID 22052078[4-(2-Chloro-4-dimethylamino-5-fluoro-phenyl)-3-nitro-pyridin-2-yl]-(1-cyclopropyl-propyl)-amineHCID 43835034Tin dichloride dihydrate

Product 1

HCID 696579484-(2-chloro-4-dimethylamino-5-fluoro-phenyl)-N2-(1-cyclopropyl-propyl)-pyridine-2,3-diamineYield 100.1%

Procedure

[4-(2-Chloro-4-dimethylamino-5-fluoro-phenyl)-3-nitro-pyridin-2-yl]-(1-cyclopropyl-propyl)-amine (300 mg, 0.76 mmol) and SnCl2.H2O (1.2 g, 6.1 mmol) were treated substantially as described in Part D of Example 74a to yield 276 mg of crude 4-(2-chloro-4-dimethylamino-5-fluoro-phenyl)-N2-(1-cyclopropyl-propyl)-pyridine-2,3-diamine: MS (EI) m/z 363.24 [(M+H)+, 100].

Sources & evidence

ORD record
ord-01ba4f9e374e4d56b359432109e06383
Source dataset
uspto-grants-2006_06
Patent number
US07067658B2

Reaction notes

Loading…