Sodium Hydroxide → HCID 69561855, compound

HRID 1890647Notes

Reaction equation

HRID 1890647 reaction equation
[CH2:1]([C:3]1[N:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][CH2:22][CH:23]3[CH2:28][CH2:27][C:26](=O)[CH2:25][CH2:24]3)=[CH:17][CH:16]=2)[C:6]2=[N:7][C:8]([CH3:12])=[CH:9][C:10]([CH3:11])=[C:5]2[N:4]=1)[CH3:2].[CH3:30][N:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+].C(O)(=O)/C=C/C(O)=O>ClCCCl.C1COCC1>[CH2:1]([C:3]1[N:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][CH2:22][CH:23]3[CH2:28][CH2:27][CH:26]([N:34]4[CH2:35][CH2:36][N:31]([CH3:30])[CH2:32][CH2:33]4)[CH2:25][CH2:24]3)=[CH:17][CH:16]=2)[C:6]2=[N:7][C:8]([CH3:12])=[CH:9][C:10]([CH3:11])=[C:5]2[N:4]=1)[CH3:2]

Participants

8

Reactant 5

HCID 14798Sodium HydroxideHCID 531671-MethylpiperazineHCID 444972Fumaric AcidHCID 5049666Sodium triacetoxyborohydrideHCID 23156210HCID 23156210, compound

Product 1

HCID 69561855HCID 69561855, compoundYield 68.8%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Compound 148 (110 mg, 0.282 mmol) was dissolved in 1,2-dichloroethane (2.8 mL) and 1-methylpiperazine (0.625 mL, 0.563 mmol) and sodium triacetoxyborohydride (119 mg, 0.563 mmol) were added to the solution, followed by stirring at room temperature for 4 hours. The reaction mixture was added with a 2 mol/L aqueous sodium hydroxide solution and extracted with ethyl acetate three times. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (2 mol/L ammonia-methanol solution:chloroform=1:19). The obtained compound was dissolved in THF, and the solution was added with a solution of fumaric acid (68.7 mg, 0.592 mmol) in THF. The precipitates were collected by filtration to obtain Compound 150 (137 mg, 0.194 mmol, 68.8%).

Workup

  1. extractionextracted with ethyl acetate three times
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (2 mol/L ammonia-methanol solution:chloroform=1:19)
  6. dissolutionThe obtained compound was dissolved in THF
  7. filtrationThe precipitates were collected by filtration

Sources & evidence

ORD record
ord-08c748c0a4fa4f6abc5fbc1bed1840ca
Source dataset
uspto-grants-2013_08
Patent number
US08507484B2

Reaction notes

Loading…