Hydrochloric Acid → N-(4-Fluoro-3-chloro-phenyl)-2-[N-methyl-N-(2,2-difluoroethyl)-amino]-4-methylamino-5-nitro-benzoic acid amide

HRID 1189633Notes

Reaction equation

HRID 1189633 reaction equation
[F:1][CH:2]([F:6])[CH2:3][NH:4][CH3:5].Cl.CCN(C(C)C)C(C)C.[F:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:38])[C:26]2[CH:31]=[C:30]([N+:32]([O-:34])=[O:33])[C:29]([NH:35][CH3:36])=[CH:28][C:27]=2F)=[CH:20][C:19]=1[Cl:39]>CC#N>[F:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:38])[C:26]2[CH:31]=[C:30]([N+:32]([O-:34])=[O:33])[C:29]([NH:35][CH3:36])=[CH:28][C:27]=2[N:4]([CH3:5])[CH2:3][CH:2]([F:6])[F:1])=[CH:20][C:19]=1[Cl:39]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 233232502,2-difluoro-N-methylethanamineHCID 67957648N-(4-Fluoro-3-chloro-phenyl)-2-fluoro-4-methylamino-5-nitro-benzoic acid amide

Product 1

HCID 86666463N-(4-Fluoro-3-chloro-phenyl)-2-[N-methyl-N-(2,2-difluoroethyl)-amino]-4-methylamino-5-nitro-benzoic acid amide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of N-(2,2-difluoroethyl)-N-methyl-amine×HCl (64 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 two weeks at reflux. Then the mixture is concentrated, diluted with EtOAc, washed with water, dried with Na2SO4 and concentrated and directly used in the next step.

Workup

  1. temperatureat reflux
  2. concentrationThen the mixture is concentrated
  3. additiondiluted with EtOAc
  4. washwashed with water
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-95e76a4fbdac4df9a635710c329bcbf1
Source dataset
uspto-grants-2014_03
Patent number
US08674113B2

Reaction notes

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