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

HRID 1831591Notes

Reaction equation

HRID 1831591 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]([CH3:23])[CH2:20][O:21][CH3:22])[C:13]=1[N+:24]([O-])=O.Cl[Sn]Cl.O>>[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]([CH3:23])[CH2:20][O:21][CH3:22])[C:13]=1[NH2:24]

Participants

3

Reactant 2

HCID 22052192[4-(2-Chloro-4-dimethylamino-5-fluoro-phenyl)-3-nitro-pyridin-2-yl]-(2-methoxy-1-methyl-ethyl)-amineHCID 43835034Tin dichloride dihydrate

Product 1

HCID 696581514-(2-chloro-4-dimethylamino-5-fluoro-phenyl)-N2-(2-methoxy-1-methyl-ethyl)-pyridine-2,3-diamineYield 99%

Procedure

[4-(2-Chloro-4-dimethylamino-5-fluoro-phenyl)-3-nitro-pyridin-2-yl]-(2-methoxy-1-methyl-ethyl)-amine (318 mg, 0.83 mmol) and SnCl2.H2O (472 mg, 2.5 mmol) were treated substantially as described in Part D of Example 74a to yield 290 mg of crude 4-(2-chloro-4-dimethylamino-5-fluoro-phenyl)-N2-(2-methoxy-1-methyl-ethyl)-pyridine-2,3-diamine: MS (EI) m/z 353.23 [(M+H)+, 100].

Sources & evidence

ORD record
ord-3056efa697b3460482024390443bc2cf
Source dataset
uspto-grants-2006_06
Patent number
US07067658B2

Reaction notes

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