1-Methoxypropan-2-amine hydrochloride → [4-(2-Chloro-4-dimethylamino-5-fluoro-phenyl)-3-nitro-pyridin-2-yl]-(2-methoxy-1-methyl-ethyl)-amine

HRID 1831590Notes

Reaction equation

HRID 1831590 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.[CH3:37][O:38][CH2:39][CH:40]([NH2:42])[CH3:41]>>[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:42][CH:40]([CH3:41])[CH2:39][O:38][CH3:37])[C:20]=1[N+:33]([O-:35])=[O:34]

Participants

3

Reactant 2

HCID 214613791-Methoxypropan-2-amine hydrochlorideHCID 131725817Trifluoro-methanesulfonic acid 4-(2-chloro-4-dimethylamino-5-fluoro-phenyl)-3-nitro-pyridin-2-yl ester TFA

Product 1

HCID 22052192[4-(2-Chloro-4-dimethylamino-5-fluoro-phenyl)-3-nitro-pyridin-2-yl]-(2-methoxy-1-methyl-ethyl)-amineYield 48.9%

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 2-methoxy-1-methyl-ethylamine HCl (208 mg, 1.7 mmol) were treated substantially as described in Part C of Example 19a to produce 318 mg of crude [4-(2-chloro-4-dimethylamino-5-fluoro-phenyl)-3-nitro-pyridin-2-yl]-(2-methoxy-1-methyl-ethyl)-amine.

Sources & evidence

ORD record
ord-79fc23abcdb34d91aaf45c89f876c851
Source dataset
uspto-grants-2006_06
Patent number
US07067658B2

Reaction notes

Loading…