Dimethylamine → (4-{[4-(4-Chlorophenyl)-pyrimidin-2-yl]amino}phenyl)-N,N-dimethyl carboxamide

HRID 33451Notes

Reaction equation

HRID 33451 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]3[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][CH:16]=3)[N:9]=2)=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH3:28][NH:29][CH3:30].C(N(CC)CC)C>C1COCC1.O.CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]3[CH:23]=[CH:22][C:18]([C:19]([N:29]([CH3:30])[CH3:28])=[O:21])=[CH:17][CH:16]=3)[N:9]=2)=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 674DimethylamineHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 219060074-{[4-(4-Chlorophenyl)pyrimidin-2-yl]amino} benzoic acid

Product 1

HCID 9975339(4-{[4-(4-Chlorophenyl)-pyrimidin-2-yl]amino}phenyl)-N,N-dimethyl carboxamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To 4-{[4-(4-chlorophenyl)pyrimidin-2-yl]amino}benzoic acid (200 mg, 0.615 mmol) is added thionyl chloride (4 mL) along with a catalytic amount of DMF at room temperature. The resulting suspension is then refluxed for a period of 1 hour resulting in a clear pale yellow solution which was concentrated in vacuo. To the flask was then added a solution of dimethylamine (615 μL of a 2.0 M solution in THF, 1.23 mmol) and triethylamine (124 mg, 1.23 mmol) in tetrahydrofuran (4.5 mL). The solution was then stirred for 18 hours at room temperature, diluted with water (5 mL) and filtered. Purification of the remaining solid by preparative HPLC yielded the title compound. HPLC/ES-MS: RT 6.74 min.(Method A); (m/z) 353 [M+1]+.

Workup

  1. temperatureThe resulting suspension is then refluxed for a period of 1 hour
  2. customresulting in a clear pale yellow solution which
  3. concentrationwas concentrated in vacuo
  4. filtrationfiltered
  5. customPurification of the remaining solid by preparative HPLC

Sources & evidence

ORD record
ord-4d3dd111dc1c446fadb7c6bd384f572e
Source dataset
uspto-grants-2008_09
Patent number
US07429599B2

Reaction notes

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