Stannous Chloride → 4-(5-chloro-4-methoxy-2-methyl-phenyl)-N2-(1-cyclopropyl-propyl)-pyridine-2,3-diamine

HRID 1831579Notes

Reaction equation

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

Participants

Reactant 2

HCID 24479Stannous Chloride

HCID 22052140(1-Cyclopropyl-propyl)-[4-(5-fluoro-4-methoxy-2-methyl-phenyl)-3-nitro-pyridin-2-yl]-amine

Product 1

HCID 696586124-(5-chloro-4-methoxy-2-methyl-phenyl)-N2-(1-cyclopropyl-propyl)-pyridine-2,3-diamineYield 102%

Procedure

(1-Cyclopropyl-propyl)-[4-(5-fluoro-4-methoxy-2-methyl-phenyl)-3-nitro-pyridin-2-yl]-amine (0.13 g, 0.34 mmol) and SnCl2 (0.19 g, 1.0 mmol) were treated substantially as described in Part D of Example 74a to yield 0.12 g (96%) of 4-(5-chloro-4-methoxy-2-methyl-phenyl)-N2-(1-cyclopropyl-propyl)-pyridine-2,3-diamine.

Sources & evidence

ORD record: ord-690f5c4acb0d4bd09c3f3f3ff2af51b8
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07067658B2

Reaction notes

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