Sodium Bicarbonate → HCID 23155992, compound

HRID 1714773Notes

Reaction equation

HRID 1714773 reaction equation
Cl.O1CCOCC1.[NH2:8][N:9]1[C:14](=[O:15])[C:13]2[CH2:16][N:17](C(OC(C)(C)C)=O)[CH2:18][CH2:19][C:12]=2[N:11]=[C:10]1[CH2:27][CH2:28][CH2:29][CH2:30][N:31]1[CH2:36][CH2:35][N:34]([C:37]2[CH:46]=[CH:45][C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[N:38]=2)[CH2:33][CH2:32]1.C(=O)([O-])O.[Na+]>>[NH2:8][N:9]1[C:14](=[O:15])[C:13]2[CH2:16][NH:17][CH2:18][CH2:19][C:12]=2[N:11]=[C:10]1[CH2:27][CH2:28][CH2:29][CH2:30][N:31]1[CH2:32][CH2:33][N:34]([C:37]2[CH:46]=[CH:45][C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[N:38]=2)[CH2:35][CH2:36]1

Participants

4

Reactant 3

HCID 516892Sodium BicarbonateHCID 204431481,4-Dioxane hydrochlorideHCID 23155731HCID 23155731, compound

Product 1

HCID 23155992HCID 23155992, compoundYield 90.6%

Procedure

To 10 ml of 4N-hydrochloric acid-dioxane solution, 53 mg of 3-amino-6-tert-butoxycarbonyl-2-[4-(4-quinolin-2-ylpiperazin-1-yl)butyl]-5,6,7,8-tetrahydro-3H-pyrido[4,3-d]pyrimidin-4-one as synthesized in above Step 4-44-A was added and stirred for 18 hours at room temperature. The solution was neutralized with saturated aqueous sodium hydrogencarbonate solution, extracted with ethyl acetate, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified on silica gel column chromatography (chloroform:methanol=9:1) to provide 39 mg (90%) of 3-amino-2-[4-(4-quinolin-2-ylpiperazin-1-yl)butyl]-5,6,7,8-tetrahydro-3H-pyrido[4,3-d]pyrimidin-4-one.

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified on silica gel column chromatography (chloroform:methanol=9:1)

Sources & evidence

ORD record
ord-0515d7410b7f4120b204347ad7bdfa4d
Source dataset
uspto-grants-2010_09
Patent number
US07799775B2

Reaction notes

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