Triethylamine → N-(2-amino-5-pyrimidinyl)-2-methyl-3-(((3-(trifluoromethyl)phenyl)carbonyl)amino)benzamide

HRID 2355094Notes

Reaction equation

HRID 2355094 reaction equation
[NH2:1][C:2]1[C:3]([CH3:18])=[C:4]([CH:15]=[CH:16][CH:17]=1)[C:5]([NH:7][C:8]1[CH:9]=[N:10][C:11]([NH2:14])=[N:12][CH:13]=1)=[O:6].CC1C=CC=CC=1C(N)=O.NC1C=CC(C)=C(C=1)C(NC1C=NC(N)=NC=1)=O.[F:47][C:48]([F:59])([F:58])[C:49]1[CH:50]=[C:51]([CH:55]=[CH:56][CH:57]=1)[C:52](Cl)=[O:53].CCN(CC)CC>C(Cl)Cl.N1C=CC=CC=1>[NH2:14][C:11]1[N:10]=[CH:9][C:8]([NH:7][C:5](=[O:6])[C:4]2[CH:15]=[CH:16][CH:17]=[C:2]([NH:1][C:52]([C:51]3[CH:55]=[CH:56][CH:57]=[C:49]([C:48]([F:47])([F:58])[F:59])[CH:50]=3)=[O:53])[C:3]=2[CH3:18])=[CH:13][N:12]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 752573-(Trifluoromethyl)benzoyl chlorideHCID 593819003-amino-N-(2-aminopyrimidin-5-yl)-2-methylbenzamideHCID 68454610methylbenzamide 5-amino-N-(2-aminopyrimidin-5-yl)-2-methylbenzamide

Product 1

HCID 16118606N-(2-amino-5-pyrimidinyl)-2-methyl-3-(((3-(trifluoromethyl)phenyl)carbonyl)amino)benzamide

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

3-amino-N-(2-aminopyrimidin-5-yl)-2-methylbenzamide 42 (113 mg, 0.464 mmol) [prepared according to the procedure described for methylbenzamide-5-amino-N-(2-aminopyrimidin-5-yl)-2-methylbenzamide in Example 1] was taken up in CH2Cl2 (4 mL) and pyridine (3 mL) and 3-(trifluoromethyl)benzoyl chloride (0.31 mL, 2.09 mmol) was added followed by NEt3 (0.13 mL, 0.928 mmol). Complete consumption of the amine starting material was indicated by LCMS. The crude reaction mixture was concentrated and the product purified using automated medium pressure chromatography (Isco—40 g column; eluting with a linear gradient from 97% CH2Cl2 (A line) to 100% 90/10/1 CH2Cl2/MeOH/NH3 (B line) on silica gel) to afford N-(2-amino-5-pyrimidinyl)-2-methyl-3-(((3-(trifluoromethyl)phenyl)carbonyl)amino)benzamide 43 as an off-white solid. MS m/z found 416 [MH+]; calc. for C20H16F3N5O2=415.13; and 2-methyl-3-(((3-(trifluoromethyl)phenyl)carbonyl)amino)-N-(2-(((3-(trifluoromethyl)phenyl)carbonyl)amino)-5-pyrimidinyl)benzamide 44 as an off-white solid. MS m/z found 588 [MH+]; calc. for C28H19F6N5O3=587.14.

Workup

  1. customComplete consumption of the amine starting material
  2. customThe crude reaction mixture
  3. concentrationwas concentrated
  4. customthe product purified
  5. washeluting with a linear gradient from 97% CH2Cl2 (A line) to 100% 90/10/1 CH2Cl2/MeOH/NH3 (B line) on silica gel)

Sources & evidence

ORD record
ord-f170aede86d94cfd8ebee2cebfa42075
Source dataset
uspto-grants-2010_07
Patent number
US07754717B2

Reaction notes

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