3-(Trifluoromethyl)benzoyl chloride → HCID 11584925, compound

HRID 1038734Notes

Reaction equation

HRID 1038734 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:29])=[C:6]([NH:8][C:9](=[O:28])[N:10]([C:12]2[CH:17]=[C:16]([NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([N:25]([CH3:27])[CH3:26])[CH:20]=3)[N:15]=[CH:14][N:13]=2)[CH3:11])[CH:7]=1.[F:30][C:31]([F:42])([F:41])[C:32]1[CH:33]=[C:34]([CH:38]=[CH:39][CH:40]=1)[C:35](Cl)=[O:36].CC[N:45](C(C)C)C(C)C>CN(C=O)C>[CH3:26][N:25]([CH3:27])[C:21]1[CH:20]=[C:19]([NH:18][C:16]2[N:15]=[CH:14][N:13]=[C:12]([N:10]([CH3:11])[C:9](=[O:28])[NH:8][C:6]3[CH:7]=[C:2]([C:33]4[C:32]([C:31]([F:42])([F:41])[F:30])=[CH:40][CH:39]=[CH:38][C:34]=4[C:35]([NH2:45])=[O:36])[CH:3]=[CH:4][C:5]=3[CH3:29])[CH:17]=2)[CH:24]=[CH:23][CH:22]=1.[CH3:26][N:25]([CH3:27])[C:21]1[CH:20]=[C:19]([NH:18][C:16]2[N:15]=[CH:14][N:13]=[C:12]([N:10]([CH3:11])[C:9](=[O:28])[NH:8][C:6]3[CH:7]=[C:2]([NH:1][C:35](=[O:36])[C:34]4[CH:38]=[CH:39][CH:40]=[C:32]([C:31]([F:30])([F:41])[F:42])[CH:33]=4)[CH:3]=[CH:4][C:5]=3[CH3:29])[CH:17]=2)[CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 752573-(Trifluoromethyl)benzoyl chlorideHCID 81531DiisopropylethylamineHCID 66669950HCID 66669950, compound

Product 2

HCID 11584925HCID 11584925, compoundHCID 86630720HCID 86630720, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(5-Amino-2-methyl-phenyl)-1-[6-(3-dimethylamino-phenylamino)-pyrimidin-4-yl]-1-methyl-urea (0.26 mmol), 3-trifluoromethyl-benzoyl chloride (57 mg, 0.27 mmol) and DIEA (68 uL, 0.39 mmol) are dissolved in 10 mL anhydrous DMF. The reaction is stirred in the room temperature for 4 hours. After removing the solvent, the crude product is dissolved into DMSO and purified by reverse phase preparative HPLC to give the final product N-(3-{3-[6-(3-Dimethylamino-phenylamino)-pyrimidin-4-yl]-3-methyl-ureido}-4-methyl-phenyl)-3-trifluoromethyl-benzamide as the white solid; 1H NMR (600 MHz, DMSO-d6) δ 12.67 (s, 1H), 10.44 (s, 1H), 9.84 (s, 1H), 8.56 (s, 1H), 8.40 (d, J=11.8 Hz, 2H), 8.28 (s, 1H), 8.24 (d, J=8.2 Hz, 1H), 7.94 (d, J=7.7 Hz, 1H), 7.76 (t, J=7.8 Hz, 1H), 7.48 (d, J=8.4 Hz, 1H), 7.35 (t, J=8.1 Hz, 1H), 7.22 (d, J=8.8 Hz, 1H), 6.81 (d, J=7.5 Hz, 1H), 6.64 (s, 1H), 6.59 (d, J=8.2 Hz, 1H), 3.35 (s, 3H), 2.92 (s, 6H), 2.35 (s, 3H); ESIMS m/z 565.3 (M++1).

Workup

  1. customAfter removing the solvent
  2. dissolutionthe crude product is dissolved into DMSO
  3. custompurified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-8759c92396fa48208e446738dd348cd4
Source dataset
uspto-grants-2013_10
Patent number
US08552002B2

Reaction notes

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