1,2-Ethanediamine, N1,N1,N2-trimethyl- → HCID 58587972, compound

HRID 446329Notes

Reaction equation

HRID 446329 reaction equation
F[C:2]1[CH:32]=[CH:31][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]3[C:21]([C:22]4[CH:27]=[CH:26][N:25]=[C:24]([NH:28][CH3:29])[N:23]=4)=[CH:20][CH:19]=[CH:18][N:17]=3)=[C:11]([CH3:30])[CH:10]=2)=[O:7])=[CH:4][C:3]=1[C:33]([F:36])([F:35])[F:34].[CH3:37][N:38]([CH3:43])[CH2:39][CH2:40][NH:41][CH3:42]>CN(C=O)C.C(OCC)(=O)C>[CH3:37][N:38]([CH3:43])[CH2:39][CH2:40][N:41]([CH3:42])[C:2]1[CH:32]=[CH:31][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]3[C:21]([C:22]4[CH:27]=[CH:26][N:25]=[C:24]([NH:28][CH3:29])[N:23]=4)=[CH:20][CH:19]=[CH:18][N:17]=3)=[C:11]([CH3:30])[CH:10]=2)=[O:7])=[CH:4][C:3]=1[C:33]([F:34])([F:36])[F:35]

Participants

5

Reactant 2

HCID 673381,2-Ethanediamine, N1,N1,N2-trimethyl-3×HCID 58588432HCID 58588432, compound

Product 1

HCID 58587972HCID 58587972, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-fluoro-N-(3-methyl-4-(3-(2-(methylamino)pyrimidin-4-yl)pyridin-2-yloxy)phenyl)-3-(trifluoromethyl)benzamide (0.10 g, 0.22 mmol) and N1,N1,N2-trimethylethane-1,2-diamine (0.045 g, 0.44 mmol) in DMF (2 mL) was heated to 100 deg. C. for 48 h. Additional N1,N1,N2-trimethylethane-1,2-diamine (0.045 g, 0.44 mmol) was added, and the reaction heated for 6 h. Additional N1,N1,N2-trimethylethane-1,2-diamine (0.045 g, 0.44 mmol) was added, and the reaction heated for 48 h. The reaction was cooled to ambient temperature, was diluted with ethyl acetate, and washed with saturated aqueous sodium bicarbonate. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to give a solid. Purification by reverse-phase HPLC using acetonitrile/water/TFA as eluent gave 4-((2-(dimethylamino)ethyl)(methyl)amino)-N-(3-methyl-4-(3-(2-(methylamino)pyrimidin-4-yl)pyridin-2-yloxy)phenyl)-3-(trifluoromethyl)benzamide as a white solid. MS m/z=580 [M+1]+. Calc'd for C30H32F3N7O2: 579.62.

Workup

  1. temperaturethe reaction heated for 6 h
  2. temperaturethe reaction heated for 48 h
  3. washwashed with saturated aqueous sodium bicarbonate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a solid
  8. customPurification by reverse-phase

Sources & evidence

ORD record
ord-bea20c33b40e47fba14906c93c455e70
Source dataset
uspto-grants-2013_07
Patent number
US08476434B2

Reaction notes

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