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

HRID 1361684Notes

Reaction equation

HRID 1361684 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-c1a48526cfc64d7bae2f4e9526008e89
Source dataset
uspto-grants-2011_02
Patent number
US07880000B2

Reaction notes

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