Sodium Bicarbonate → HCID 23155938, compound

HRID 1714767Notes

Reaction equation

HRID 1714767 reaction equation
N[N:2]1[C:7](=[O:8])[C:6]2[C:9]3[CH2:15][CH2:14][N:13]([C:16]([O:18]C(C)(C)C)=O)[CH2:12][C:10]=3[S:11][C:5]=2[N:4]=[C:3]1[CH2:23][CH2:24][CH2:25][CH2:26][N:27]1[CH2:32][CH2:31][N:30]([C:33]2[CH:42]=[CH:41][C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[N:34]=2)[CH2:29][CH2:28]1.N([O-])=O.[Na+].[C:47](=O)([O-])O.[Na+]>C(O)(=O)C.O>[C:16]([N:13]1[CH2:14][CH2:15][C:9]2[C:6]3[C:7](=[O:8])[NH:2][C:3]([CH2:23][CH2:24][CH2:25][CH2:26][N:27]4[CH2:28][CH2:29][N:30]([C:33]5[CH:42]=[CH:41][C:40]6[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=6)[N:34]=5)[CH2:31][CH2:32]4)=[N:4][C:5]=3[S:11][C:10]=2[CH2:12]1)(=[O:18])[CH3:47]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 23155611HCID 23155611, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 23155938HCID 23155938, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

In a mixture of 5 ml of acetic acid with 2 ml of water 60 mg of 3-amino-7-tert-butoxycarbonyl-2-[4-(4-quinolin-2-ylpiperazin-1-yl)butyl]-5,6,7,8-tetrahydro-3H-pyrido[4′3′:4,5]thieno[2,3-d]pyrimidin-4-one was dissolved, and into the solution, a solution of 10 mg of sodium nitrite in 2 ml of water was dropped under cooling with ice. After 30 minutes' stirring, the reaction mixture was neutralized with saturated aqueous sodium hydrogencarbonate solution, and the resulting precipitate was extracted with chloroform, washed with water and dried over anhydrous sodium sulfate. Distilling the solvent off under reduced pressure, the residue was purified on silica gel column chromatography to provide 52 mg (99%) of 7-acetyl-2-[4-(4-quinolin-2-ylpiperazin-1-yl)butyl]-5,6,7,8-tetrahydro-3H-pyrido[4′3′:4,5]thieno-[2,3-d]pyrimidin-4-one.

Workup

  1. dissolutionwas dissolved
  2. temperatureunder cooling with ice
  3. extractionthe resulting precipitate was extracted with chloroform
  4. washwashed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationDistilling the solvent off under reduced pressure
  7. customthe residue was purified on silica gel column chromatography

Sources & evidence

ORD record
ord-55dcbdf9cd3e45e79f5325f9bd2e0c44
Source dataset
uspto-grants-2010_09
Patent number
US07799775B2

Reaction notes

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