Tin dichloride dihydrate → (R)-4-(2-chloro-4-dimethylamino-5-fluoro-phenyl)-N2-(1-cyclopropyl-ethyl)-pyridine-2,3-diamine

HRID 1831587Notes

Reaction equation

HRID 1831587 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][C@@H:19]([CH:21]2[CH2:23][CH2:22]2)[CH3:20])[C:13]=1[N+:24]([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][C@@H:19]([CH:21]2[CH2:22][CH2:23]2)[CH3:20])[C:13]=1[NH2:24]

Participants

3

Reactant 2

HCID 43835034Tin dichloride dihydrateHCID 69658051(R)-[4-(2-Chloro-4-dimethylamino-5-fluoro-phenyl)-3-nitro-pyridin-2-yl]-(1-cyclopropyl-ethyl)-amine

Product 1

HCID 69658225(R)-4-(2-chloro-4-dimethylamino-5-fluoro-phenyl)-N2-(1-cyclopropyl-ethyl)-pyridine-2,3-diamineYield 95.3%

Procedure

(R)-[4-(2-Chloro-4-dimethylamino-5-fluoro-phenyl)-3-nitro-pyridin-2-yl]-(1-cyclopropyl-ethyl)-amine (314 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 276 mg of crude (R)-4-(2-chloro-4-dimethylamino-5-fluoro-phenyl)-N2-(1-cyclopropyl-ethyl)-pyridine-2,3-diamine: MS (EI) m/z 349.24 [(M+H)+, 100].

Sources & evidence

ORD record
ord-c2aec4ceb16e4b89b9f3a7cda1f3b640
Source dataset
uspto-grants-2006_06
Patent number
US07067658B2

Reaction notes

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