(1R)-1-cyclobutylethan-1-amine hydrochloride → (R)-[4-(2-Chloro-4-dimethylamino-5-fluoro-phenyl)-3-nitro-pyridin-2-yl]-(1-cyclobutyl-ethyl)-amine

HRID 1831588Notes

Reaction equation

HRID 1831588 reaction equation
OC(C(F)(F)F)=O.[Cl:8][C:9]1[CH:14]=[C:13]([N:15]([CH3:17])[CH3:16])[C:12]([F:18])=[CH:11][C:10]=1[C:19]1[CH:24]=[CH:23][N:22]=[C:21](OS(C(F)(F)F)(=O)=O)[C:20]=1[N+:33]([O-:35])=[O:34].Cl.[CH:37]1([C@H:41]([NH2:43])[CH3:42])[CH2:40][CH2:39][CH2:38]1>>[Cl:8][C:9]1[CH:14]=[C:13]([N:15]([CH3:17])[CH3:16])[C:12]([F:18])=[CH:11][C:10]=1[C:19]1[CH:24]=[CH:23][N:22]=[C:21]([NH:43][C@@H:41]([CH:37]2[CH2:40][CH2:39][CH2:38]2)[CH3:42])[C:20]=1[N+:33]([O-:35])=[O:34]

Participants

3

Reactant 2

HCID 69658276(1R)-1-cyclobutylethan-1-amine hydrochlorideHCID 131725817Trifluoro-methanesulfonic acid 4-(2-chloro-4-dimethylamino-5-fluoro-phenyl)-3-nitro-pyridin-2-yl ester TFA

Product 1

HCID 69658117(R)-[4-(2-Chloro-4-dimethylamino-5-fluoro-phenyl)-3-nitro-pyridin-2-yl]-(1-cyclobutyl-ethyl)-amineYield 48.8%

Procedure

Trifluoro-methanesulfonic acid 4-(2-chloro-4-dimethylamino-5-fluoro-phenyl)-3-nitro-pyridin-2-yl ester TFA (1.1 g, 2.49 mmol) and (R)-1-cyclobutyl-ethylamine HCl (225 mg, 1.7 mmol) were treated substantially as described in Part C of Example 19a to produce 326 mg of crude (R)-[4-(2-Chloro-4-dimethylamino-5-fluoro-phenyl)-3-nitro-pyridin-2-yl]-(1-cyclobutyl-ethyl)-amine.

Sources & evidence

ORD record
ord-2a6fabfd6cfc4fde9d92995d3fc837aa
Source dataset
uspto-grants-2006_06
Patent number
US07067658B2

Reaction notes

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