Sodium borohydride → HCID 23155899, compound

HRID 1714775Notes

Reaction equation

HRID 1714775 reaction equation
[BH4-].[Na+].[CH2:3]1[CH2:41][O:40][C:5]2([CH2:14][CH2:13][C:12]3[N:11]=[C:10]([CH2:15][CH2:16][CH2:17][CH2:18][N:19]4[CH2:24][CH2:23][N:22]([C:25]5[CH:34]=[CH:33][C:32]6[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=6)[N:26]=5)[CH2:21][CH2:20]4)[N:9]([N:35]=[C:36]([CH3:38])[CH3:37])[C:8](=[O:39])[C:7]=3[CH2:6]2)[O:4]1>CO>[CH2:41]1[CH2:3][O:4][C:5]2([CH2:14][CH2:13][C:12]3[N:11]=[C:10]([CH2:15][CH2:16][CH2:17][CH2:18][N:19]4[CH2:24][CH2:23][N:22]([C:25]5[CH:34]=[CH:33][C:32]6[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=6)[N:26]=5)[CH2:21][CH2:20]4)[N:9]([NH:35][CH:36]([CH3:37])[CH3:38])[C:8](=[O:39])[C:7]=3[CH2:6]2)[O:40]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 23155961HCID 23155961, compound

Product 1

HCID 23155899HCID 23155899, compoundYield 61.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To 10 ml of methanol, 300 mg of sodium borohydride was added and into this mixture, a solution of 145 mg of 6,6-ethylenedioxy-3-isopropylideneamino-2-[4-(4-quinolin-2-ylpiperazin-1-yl)butyl]-5,6,7,8-tetrahydro-3H-quinazolin-4-one as synthesized in Example 4-67 in 10 ml of methanol was dropped under cooling with ice. Raising the temperature to room temperature, the reaction mixture was stirred for an hour. Distilling the system under reduced pressure, water was added to the distillation residue, extracted with methylene chloride, washed with water, dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was purified on silica gel column chromatography (methanol:methylene chloride=2:23) to provide 89 mg (61%) of 6,6-ethylenedioxy-3-isopropylamino-2-[4-(4-quinolin-2-ylpiperazin-1-yl)butyl]-5,6,7,8-tetrahydro-3H-quinazolin-4-one.

Workup

  1. additionwas dropped
  2. temperatureunder cooling with ice
  3. distillationDistilling the system under reduced pressure, water
  4. additionwas added to the distillation residue
  5. extractionextracted with methylene chloride
  6. washwashed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue was purified on silica gel column chromatography (methanol:methylene chloride=2:23)

Sources & evidence

ORD record
ord-58697b6245034250ba62f0491dbe5b6a
Source dataset
uspto-grants-2010_09
Patent number
US07799775B2

Reaction notes

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