Methanesulfonic Acid → 3-[1-(6-Amino-pyrimidin-4-yl)-1H-benzoimidazol-2-ylamino]-4-methyl-N-[4-(2-methyl-imidazol-1-yl)-3-trifluoromethyl-phenyl]-benzamide

HRID 1968422Notes

Reaction equation

HRID 1968422 reaction equation
Cl[C:2]1[N:6]([C:7]2[N:12]=[CH:11][N:10]=[C:9]([NH2:13])[CH:8]=2)[C:5]2[CH:14]=[CH:15][CH:16]=[CH:17][C:4]=2[N:3]=1.[NH2:18][C:19]1[CH:20]=[C:21]([CH:41]=[CH:42][C:43]=1[CH3:44])[C:22]([NH:24][C:25]1[CH:30]=[CH:29][C:28]([N:31]2[CH:35]=[CH:34][N:33]=[C:32]2[CH3:36])=[C:27]([C:37]([F:40])([F:39])[F:38])[CH:26]=1)=[O:23].CS(O)(=O)=O>CN1CCN(C)C1=O>[NH2:13][C:9]1[N:10]=[CH:11][N:12]=[C:7]([N:6]2[C:5]3[CH:14]=[CH:15][CH:16]=[CH:17][C:4]=3[N:3]=[C:2]2[NH:18][C:19]2[CH:20]=[C:21]([CH:41]=[CH:42][C:43]=2[CH3:44])[C:22]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([N:31]3[CH:35]=[CH:34][N:33]=[C:32]3[CH3:36])=[C:27]([C:37]([F:40])([F:39])[F:38])[CH:26]=2)=[O:23])[CH:8]=1

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 598224523-amino-4-methyl-N-[4-(2-methyl-imidazol-1-yl)-3-trifluoromethyl-phenyl]-benzamideHCID 598224556-(2-Chloro-benzoimidazol-1-yl)-pyrimidin-4-ylamine

Product 1

HCID 119908193-[1-(6-Amino-pyrimidin-4-yl)-1H-benzoimidazol-2-ylamino]-4-methyl-N-[4-(2-methyl-imidazol-1-yl)-3-trifluoromethyl-phenyl]-benzamide

Reagents, catalysts & solvents 1

HCID 66611,3-Dimethyl-2-imidazolidinoneSolvent

Procedure

A solution of 6-(2-Chloro-benzoimidazol-1-yl)-pyrimidin-4-ylamine (15 mg, 0.056 mmol), 3-amino-4-methyl-N-[4-(2-methyl-imidazol-1-yl)-3-trifluoromethyl-phenyl]-benzamide (22 mg, 0.059 mmol), and MeSO3H (11.0 μL, 0.17 mmol) in 1,3-dimethyl-2-imidazolidinone (0.2 ml) is heated at 80° C. After stirring for overnight, the reaction mixture is cooled to room temperature. Purification by reverse-phase LC-MS afforded the title compound: 1H NMR 600 MHz (DMSO-d6) δ 11.50-11.00 (bs, 1H), 10.90 (s, 1H), 9.02 (s, 1H), 8.57 (s, 1H), 8.55 (d, J=2.0 Hz, 1H), 8.37 (dd, J=8.2, 2.0 Hz 1H), 7.92 (s, 1H), 7.87 (d, J=8.2 Hz, 1H), 7.81 (d, J=2.0 Hz, 1H), 7.70 (s, 1H), 7.69 (s, 1H), 7.55-7.46 (m, 4H), 7.87 (d, J=8.2 Hz, 1H), 7.27 (t, J=8.2 Hz, 1H), 7.22 (t, J=8.2 Hz, 1H), 2.46 (s, 3H), 2.41 (s, 3H); MS m/z 584.2 (M+1).

Workup

  1. customPurification by reverse-phase LC-MS

Sources & evidence

ORD record
ord-2b0ed101604f4f04b83552dd6649fa2a
Source dataset
uspto-grants-2013_04
Patent number
US08426404B2

Reaction notes

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