Diisopropylethylamine → HCID 46917286, compound

HRID 1619853Notes

Reaction equation

HRID 1619853 reaction equation
CCN(C(C)C)C(C)C.[F:10][CH:11]([F:41])[C:12]1[N:16]([C:17]2[N:22]=[C:21]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)[N:20]=[C:19]([N:29]3[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]3)[N:18]=2)[C:15]2[CH:35]=[CH:36][CH:37]=[C:38]([O:39][CH3:40])[C:14]=2[N:13]=1.[N:42]1[CH:47]=[CH:46][CH:45]=[C:44]([S:48](Cl)(=[O:50])=[O:49])[CH:43]=1>O>[F:41][CH:11]([F:10])[C:12]1[N:16]([C:17]2[N:22]=[C:21]([N:23]3[CH2:24][CH2:25][O:26][CH2:27][CH2:28]3)[N:20]=[C:19]([N:29]3[CH2:34][CH2:33][N:32]([S:48]([C:44]4[CH:43]=[N:42][CH:47]=[CH:46][CH:45]=4)(=[O:50])=[O:49])[CH2:31][CH2:30]3)[N:18]=2)[C:15]2[CH:35]=[CH:36][CH:37]=[C:38]([O:39][CH3:40])[C:14]=2[N:13]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 3164136Pyridine-3-sulfonyl chlorideHCID 666980472-(difluoromethyl)-4-methoxy-1-[4-(4-morpholinyl)-6-(1-piperazinyl)-1,3,5-triazin-2-yl]-1H-benzimidazole

Product 1

HCID 46917286HCID 46917286, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

DIPEA (0.78 mL, 4.48 mmol) was added to a mixture of 2-(difluoromethyl)-4-methoxy-1-[4-(4-morpholinyl)-6-(1-piperazinyl)-1,3,5-triazin-2-yl]-1H-benzimidazole (Example 2) (200 mg, 0.449 mmol) and 3-pyridinesulfonyl chloride (159 mg, 0.859 mmol) at room temperature under nitrogen. The reaction mixture was stirred at room temperature for 18.5 hrs. Water was added and the phases were separated. The organic phase was dried (Na2SO4) and the solvent was removed under vacuum. Chromatography on silica, eluting with CH2Cl2/MeOH (99:1), gave 2-(difluoromethyl)-4-methoxy-1-{4-(4-morpholinyl)-6-[4-(3-pyridinylsulfonyl)-1-piperazinyl]-1,3,5-triazin-2-yl}-1H-benzimidazole (227 mg, 86%).

Workup

  1. customthe phases were separated
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. customthe solvent was removed under vacuum
  4. washChromatography on silica, eluting with CH2Cl2/MeOH (99:1)

Sources & evidence

ORD record
ord-d73d693643cc417eade5079d3ebcd60a
Source dataset
uspto-grants-2014_07
Patent number
US08772287B2

Reaction notes

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