3-(Dimethylamino)pyrrolidine → N-[2-Chloro-5-(2'-methylamino-[3,4']bipyridinyl-2-yloxy)-phenyl]-2-(3-dimethylamino-pyrrolidin-1-yl)-5-trifluoromethyl-benzamide

HRID 446333Notes

Reaction equation

HRID 446333 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[C:14]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]([NH:21][CH3:22])[CH:16]=3)=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:4][C:3]=1[NH:23][C:24](=[O:36])[C:25]1[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[CH:27][C:26]=1F.[CH3:37][N:38]([CH3:44])[CH:39]1[CH2:43][CH2:42][NH:41][CH2:40]1>CS(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[C:14]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]([NH:21][CH3:22])[CH:16]=3)=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:4][C:3]=1[NH:23][C:24](=[O:36])[C:25]1[CH:30]=[C:29]([C:31]([F:32])([F:33])[F:34])[CH:28]=[CH:27][C:26]=1[N:41]1[CH2:42][CH2:43][CH:39]([N:38]([CH3:44])[CH3:37])[CH2:40]1

Participants

4

Reactant 2

HCID 27585193-(Dimethylamino)pyrrolidineHCID 58588060HCID 58588060, compound

Product 1

HCID 66970539N-[2-Chloro-5-(2'-methylamino-[3,4']bipyridinyl-2-yloxy)-phenyl]-2-(3-dimethylamino-pyrrolidin-1-yl)-5-trifluoromethyl-benzamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

N-[2-Chloro-5-(2′-methylamino-[3,4′]bipyridinyl-2-yloxy)-phenyl]-2-fluoro-5-trifluoromethyl-benzamide (65 mg, 0.13 mmol) and dimethyl-pyrrolidin-3-yl-amine (22 mg, 0.189 mmol) were dissolved in 0.3 mL DMSO. The solution was heated to 80° C. and stirred for 22 h. The reaction was then cooled to RT, quenched with water, extracted into EtOAc, washed twice with water, once with brine, dried over Mg2SO4, filtered, and concentrated in vacuo to yield a crude mixture that was purified by preparative TLC (10% MeOH/CH2Cl2) to give the title compound as an off-white solid. MS m/z (M+H)+=611; Calc'd 611.06 for C31H30ClF3N6O2.

Workup

  1. temperatureThe reaction was then cooled to RT
  2. customquenched with water
  3. extractionextracted into EtOAc
  4. washwashed twice with water, once with brine
  5. dry with materialdried over Mg2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto yield a crude mixture that
  9. customwas purified by preparative TLC (10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-02d03c8b151b4203a9d625c72ad7285e
Source dataset
uspto-grants-2013_07
Patent number
US08476434B2

Reaction notes

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