(R)-1-cyclopropyl-propylamine → (R)-(1-Cyclopropyl-propyl)-[4-(5-fluoro-4-methoxy-2-methyl-phenyl)-3-nitro-pyridin-2-yl]-amine

HRID 1831542Notes

Reaction equation

HRID 1831542 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.[CH:28]1([C@H:31]([NH2:34])[CH2:32][CH3:33])[CH2:30][CH2:29]1>>[CH:28]1([C@H:31]([NH:34][C:10]2[C:9]([N+:22]([O-:24])=[O:23])=[C:8]([C:6]3[CH:7]=[C:2]([F:1])[C:3]([O:26][CH3:27])=[CH:4][C:5]=3[CH3:25])[CH:13]=[CH:12][N:11]=2)[CH2:32][CH3:33])[CH2:30][CH2:29]1

Participants

3

Reactant 2

HCID 55293659(R)-1-cyclopropyl-propylamineHCID 86591990Trifluoro-methanesulfonic acid 4-(5-fluoro-4-methoxy-2-methyl-phenyl)-3-nitro-pyridin-2-yl ester

Product 1

HCID 69658188(R)-(1-Cyclopropyl-propyl)-[4-(5-fluoro-4-methoxy-2-methyl-phenyl)-3-nitro-pyridin-2-yl]-amineYield 43%

Procedure

Trifluoro-methanesulfonic acid 4-(5-fluoro-4-methoxy-2-methyl-phenyl)-3-nitro-pyridin-2-yl ester (0.5 g, 1.22 mmol), prepared substantially as described in Part C of Example 19a, and (R)-1-cyclopropyl-propylamine (0.33 g, 2.44 mmol) were treated substantially as described in Part C of Example 19a to produce 0.17 g (43%) of crude (R)-(1-Cyclopropyl-propyl)-[4-(5-fluoro-4-methoxy-2-methyl-phenyl)-3-nitro-pyridin-2-yl]-amine.

Workup

  1. additionwere treated substantially

Sources & evidence

ORD record
ord-1a446f628b094c07b4df504fa7d7f90d
Source dataset
uspto-grants-2006_06
Patent number
US07067658B2

Reaction notes

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