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

HRID 1831583Notes

Reaction equation

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

Participants

Reactant 2

HCID 24479Stannous Chloride

HCID 22052097[4-(2-Chloro-4-methoxy-5-methyl-phenyl)-3-nitro-pyridin-2-yl]-(1-cyclopropyl-propyl)-amine

Product 1

HCID 696581364-(2-chloro-4-methoxy-5-methyl-phenyl)-N2-(1-cyclopropyl-propyl)-pyridine-2,3-diamineYield 98%

Procedure

[4-(2-Chloro-4-methoxy-5-methyl-phenyl)-3-nitro-pyridin-2-yl]-(1-cyclopropyl-propyl)-amine (90 mg, 0.24 mmol) and SnCl2 (0.13 g, 0.72 mmol) were treated substantially as described in Part D of Example 74a to yield 80 mg (98%) of 4-(2-chloro-4-methoxy-5-methyl-phenyl)-N2-(1-cyclopropyl-propyl)-pyridine-2,3-diamine: MS (EI) m/z 346.22 [(M+H)+, 100].

Sources & evidence

ORD record: ord-ba678e07a1014be3bb83b24619517c5d
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07067658B2

Reaction notes

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