Hydrochloric Acid → (R)-[4-(5-fluoro-4-methoxy-2-methyl-phenyl)-3-nitro-pyridin-2-yl]-(1-methoxymethyl-propyl)-amine

HRID 1831545Notes

Reaction equation

HRID 1831545 reaction equation
[F:1][C:2]1[C:3]([O:26][CH3:27])=[CH:4][C:5]([CH3:25])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10](OS(C(F)(F)F)(=O)=O)[C:9]=2[N+:22]([O-:24])=[O:23])[CH:7]=1.[CH3:28][O:29][CH2:30][C@H:31]([NH2:34])[CH2:32][CH3:33].Cl>>[F:1][C:2]1[C:3]([O:26][CH3:27])=[CH:4][C:5]([CH3:25])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:34][C@@H:31]([CH2:30][O:29][CH3:28])[CH2:32][CH3:33])[C:9]=2[N+:22]([O-:24])=[O:23])[CH:7]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 210356842-Butanamine, 1-methoxy-, (2R)-HCID 86591990Trifluoro-methanesulfonic acid 4-(5-fluoro-4-methoxy-2-methyl-phenyl)-3-nitro-pyridin-2-yl ester

Product 1

HCID 69658289(R)-[4-(5-fluoro-4-methoxy-2-methyl-phenyl)-3-nitro-pyridin-2-yl]-(1-methoxymethyl-propyl)-amineYield 37%

Procedure

Trifluoro-methanesulfonic acid 4-(5-fluoro-4-methoxy-2-methyl-phenyl)-3-nitro-pyridin-2-yl ester (0.5 g, 1.2 mmol), prepared substantially as described in Part C of Example 19a, and (R)-1-methoxymethyl-propylamine.HCl (0.34 g, 2.4 mmol) were treated substantially as described in Part C of Example 19a to produce 0.16 g (37%) of crude (R)-[4-(5-fluoro-4-methoxy-2-methyl-phenyl)-3-nitro-pyridin-2-yl]-(1-methoxymethyl-propyl)-amine.

Sources & evidence

ORD record
ord-6131ab5087ce47c1b8af380507c46a15
Source dataset
uspto-grants-2006_06
Patent number
US07067658B2

Reaction notes

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