1-Cyclopropylpropan-1-amine hydrochloride → [4-(2-Chloro-4-dimethylamino-5-fluoro-phenyl)-3-nitro-pyridin-2-yl]-(1-cyclopropyl-propyl)-amine

HRID 1831584Notes

Reaction equation

HRID 1831584 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](OS(C(F)(F)F)(=O)=O)[C:13]=1[N+:26]([O-:28])=[O:27].Cl.[CH:30]1([CH:33]([NH2:36])[CH2:34][CH3:35])[CH2:32][CH2:31]1>>[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:36][CH:33]([CH:30]2[CH2:32][CH2:31]2)[CH2:34][CH3:35])[C:13]=1[N+:26]([O-:28])=[O:27]

Participants

3

Reactant 2

HCID 187699371-Cyclopropylpropan-1-amine hydrochlorideHCID 86591998Trifluoro-methanesulfonic acid 4-(2-chloro-4-dimethylamino-5-fluoro-phenyl)-3-nitro-pyridin-2-yl ester

Product 1

HCID 22052078[4-(2-Chloro-4-dimethylamino-5-fluoro-phenyl)-3-nitro-pyridin-2-yl]-(1-cyclopropyl-propyl)-amineYield 43.4%

Procedure

Trifluoro-methanesulfonic acid 4-(2-chloro-4-dimethylamino-5-fluoro-phenyl)-3-nitro-pyridin-2-yl ester (548 mg, 1.76 mmol) and 1-cyclopropyl-propylamine HCl (479 mg, 3.5 mmol) were treated substantially as described in Part C of Example 19a to produce 300 mg (43%) of crude [4-(2-chloro-4-dimethylamino-5-fluoro-phenyl)-3-nitro-pyridin-2-yl]-(1-cyclopropyl-propyl)-amine: MS (EI) m/z 393.22 [(M+H)+, 100].

Sources & evidence

ORD record
ord-3caef49ec1d648a289a414f6163319eb
Source dataset
uspto-grants-2006_06
Patent number
US07067658B2

Reaction notes

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