1-(2-Hydroxyethyl)piperazine → HCID 46918342, compound

HRID 516378Notes

Reaction equation

HRID 516378 reaction equation
[F:1][CH:2]([F:37])[C:3]1[N:7]([C:8]2[N:13]=[C:12]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[N:11]=[C:10]([N:20]3[CH2:25][CH2:24][N:23]([S:26]([CH:29]=[CH2:30])(=[O:28])=[O:27])[CH2:22][CH2:21]3)[N:9]=2)[C:6]2[CH:31]=[CH:32][CH:33]=[C:34]([O:35][CH3:36])[C:5]=2[N:4]=1.[OH:38][CH2:39][CH2:40][N:41]1[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]1>O1CCOCC1>[F:37][CH:2]([F:1])[C:3]1[N:7]([C:8]2[N:13]=[C:12]([N:14]3[CH2:15][CH2:16][O:17][CH2:18][CH2:19]3)[N:11]=[C:10]([N:20]3[CH2:21][CH2:22][N:23]([S:26]([CH2:29][CH2:30][N:44]4[CH2:45][CH2:46][N:41]([CH2:40][CH2:39][OH:38])[CH2:42][CH2:43]4)(=[O:28])=[O:27])[CH2:24][CH2:25]3)[N:9]=2)[C:6]2[CH:31]=[CH:32][CH:33]=[C:34]([O:35][CH3:36])[C:5]=2[N:4]=1

Participants

4

Reactant 2

HCID 76771-(2-Hydroxyethyl)piperazineHCID 469174972-(difluoromethyl)-4-methoxy-1-{4-(4-morpholinyl)-6-[4-(vinylsulfonyl)-1-piperazinyl]-1,3,5-triazin-2-yl}-1H-benzimidazole

Product 1

HCID 46918342HCID 46918342, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-(difluoromethyl)-4-methoxy-1-{4-(4-morpholinyl)-6-[4-(vinylsulfonyl)-1-piperazinyl]-1,3,5-triazin-2-yl}-1H-benzimidazole (Example 3) (150 mg, 0.280 mmol) and N-(2-hydroxyethyl)piperazine (360 mg, 2.77 mmol) in 1,4-dioxane (15 mL) was refluxed for 3 hrs. The reaction mixture was then cooled to room temperature and the solvent was removed under vacuum. The residue was partitioned between CH2Cl2 and H2O. The phases were separated, the organic phase was dried (Na2SO4), and the solvent was removed under vacuum. Recrystallization from CH2Cl2/hexanes gave 2-{4-[2-({4-[4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-1-piperazinyl}sulfonyl)ethyl]-1-piperazinyl}ethanol (134 mg, 72%).

Workup

  1. temperaturewas refluxed for 3 hrs
  2. customthe solvent was removed under vacuum
  3. customThe residue was partitioned between CH2Cl2 and H2O
  4. customThe phases were separated
  5. dry with materialthe organic phase was dried (Na2SO4)
  6. customthe solvent was removed under vacuum
  7. customRecrystallization from CH2Cl2/hexanes

Sources & evidence

ORD record
ord-a168b72b6c594465805308c3a8c34bbf
Source dataset
uspto-grants-2015_08
Patent number
US09108980B2

Reaction notes

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