Hydrochloric Acid → N-(4-Fluoro-3-chloro-phenyl)-2-(4-fluoro-piperidinyl)-4-methylamino-5-nitro-benzoic acid amide

HRID 1189631Notes

Reaction equation

HRID 1189631 reaction equation
[F:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.Cl.CCN(C(C)C)C(C)C.[F:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26](=[O:39])[C:27]2[CH:32]=[C:31]([N+:33]([O-:35])=[O:34])[C:30]([NH:36][CH3:37])=[CH:29][C:28]=2F)=[CH:21][C:20]=1[Cl:40]>CC#N>[F:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26](=[O:39])[C:27]2[CH:32]=[C:31]([N+:33]([O-:35])=[O:34])[C:30]([NH:36][CH3:37])=[CH:29][C:28]=2[N:5]2[CH2:6][CH2:7][CH:2]([F:1])[CH2:3][CH2:4]2)=[CH:21][C:20]=1[Cl:40]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 27591594-FluoropiperidineHCID 67957648N-(4-Fluoro-3-chloro-phenyl)-2-fluoro-4-methylamino-5-nitro-benzoic acid amide

Product 1

HCID 67957338N-(4-Fluoro-3-chloro-phenyl)-2-(4-fluoro-piperidinyl)-4-methylamino-5-nitro-benzoic acid amide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-fluoropiperidine×HCl (67 mg, 0.48 mmol), DIPEA (0.64 ml, 3.73 mmol), N-(4-fluoro-3-chloro-phenyl)-2-fluoro-4-methylamino-5-nitro-benzoic acid amide (150 mg, 0.44 mmol) and MeCN (5 mL) is stirred for 6 h at reflux. Then the mixture is concentrated, diluted with EtOAc, washed with water and concentrated.

Workup

  1. temperatureat reflux
  2. concentrationThen the mixture is concentrated
  3. additiondiluted with EtOAc
  4. washwashed with water
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-22c0fe1ca3de491d9f5612c09ca658e6
Source dataset
uspto-grants-2014_03
Patent number
US08674113B2

Reaction notes

Loading…