Diisopropylethylamine → N-{3-[1-(6-Amino-pyrimidin-4-yl)-1H-benzoimidazol-2-ylamino]-4-methyl-phenyl}-3-morpholin-4-yl-5-trifluoromethyl-benzamide

HRID 1968425

Reaction equation

HRID 1968425 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([N:8]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[N:10]=[C:9]2[NH:17][C:18]2[CH:19]=[C:20]([NH2:25])[CH:21]=[CH:22][C:23]=2[CH3:24])[CH:3]=1.[N:26]1([C:32]2[CH:33]=[C:34]([CH:38]=[C:39]([C:41]([F:44])([F:43])[F:42])[CH:40]=2)[C:35](O)=[O:36])[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([N:8]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[N:10]=[C:9]2[NH:17][C:18]2[CH:19]=[C:20]([NH:25][C:35](=[O:36])[C:34]3[CH:38]=[C:39]([C:41]([F:42])([F:43])[F:44])[CH:40]=[C:32]([N:26]4[CH2:31][CH2:30][O:29][CH2:28][CH2:27]4)[CH:33]=3)[CH:21]=[CH:22][C:23]=2[CH3:24])[CH:3]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 15948950N3-[1-(6-Amino-pyrimidin-4-yl)-1H-benzoimidazol-2-yl]-4-methyl-benzene-1,3-diamineHCID 220579413-Morpholin-4-yl-5-trifluoromethyl-benzoic acid

Product 1

HCID 15950140N-{3-[1-(6-Amino-pyrimidin-4-yl)-1H-benzoimidazol-2-ylamino]-4-methyl-phenyl}-3-morpholin-4-yl-5-trifluoromethyl-benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N3-[1-(6-amino-pyrimidin-4-yl)-1H-benzoimidazol-2-yl]-4-methyl-benzene-1,3-diamine (10.0 mg, 0.030 mmol), 3-morpholin-4-yl-5-trifluoromethyl-benzoic acid (10 mg, 0.036 mmol), and DIEA (21 μL, 0.12 mmol) in DMF (2 mL) is added HATU (13 mg, 0.033 m mol). After stirring for 1 hour at room temperature, the solvent is removed under vacuum. The residue is dissolved in DMSO (1 mL). The resulting solution is subjected to purification by reverse-phase LC-MS to yield the title compound.

Workup

  1. customthe solvent is removed under vacuum
  2. dissolutionThe residue is dissolved in DMSO (1 mL)
  3. customThe resulting solution is subjected to purification by reverse-phase LC-MS

Sources & evidence

ORD record
ord-fa289010c5cd443ab8d0fbe8b31203ba
Source dataset
uspto-grants-2013_04
Patent number
US08426404B2

Linked notes

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