Acetic Acid → HCID 11621199, compound

HRID 2080836Notes

Reaction equation

HRID 2080836 reaction equation
[CH2:1]([N:4]([CH2:29][CH2:30][CH3:31])[CH2:5][CH2:6][CH2:7][CH2:8][N:9]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][NH:22][CH2:23][C:24]2[NH:25][CH:26]=[CH:27][N:28]=2)=[CH:17][CH:16]=1)[S:10]([CH3:13])(=[O:12])=[O:11])[CH2:2][CH3:3].[N:32]1[C:41]2[C:40](=O)[CH2:39][CH2:38][CH2:37][C:36]=2[CH:35]=[CH:34][CH:33]=1.C([BH3-])#N.[Na+].C(O)(=O)C>CO>[CH2:29]([N:4]([CH2:1][CH2:2][CH3:3])[CH2:5][CH2:6][CH2:7][CH2:8][N:9]([CH2:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:21][N:22]([CH2:23][C:24]2[NH:28][CH:27]=[CH:26][N:25]=2)[CH:40]2[C:41]3[N:32]=[CH:33][CH:34]=[CH:35][C:36]=3[CH2:37][CH2:38][CH2:39]2)=[CH:19][CH:20]=1)[S:10]([CH3:13])(=[O:11])=[O:12])[CH2:30][CH3:31]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 117447776,7-Dihydro-5H-quinoline-8-oneHCID 23155535HCID 23155535, compound

Product 1

HCID 11621199HCID 11621199, compoundYield 34.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (154 mg) obtained in Example 50-2 was dissolved in anhydrous methanol (6.2 ml) and added with 6,7-dihydro-5H-quinolin-8-one (75.1 mg) which was synthesized by a known method and sodium cyanoborohydride (64.1 mg). After the solution was adjusted to pH 5 with acetic acid, the whole was stirred at room temperature for 2 days. After completion of the reaction, the solvent was distilled off. The resultant was added with a 1 mol/l sodium hydroxide aqueous solution and the whole was subjected to extraction with chloroform. The resultant was dried with magnesium sulfate and the solvent was distilled off. The residue was purified through silica gel column chromatography (chloroform/ethyl acetate) and treated with hydrochloric acid, thereby obtaining a hydrochloride (69 mg) of the subject compound as a pale-yellow solid.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off
  3. additionThe resultant was added with a 1 mol/l sodium hydroxide aqueous solution
  4. extractionthe whole was subjected to extraction with chloroform
  5. dry with materialThe resultant was dried with magnesium sulfate
  6. distillationthe solvent was distilled off
  7. customThe residue was purified through silica gel column chromatography (chloroform/ethyl acetate)
  8. additiontreated with hydrochloric acid

Sources & evidence

ORD record
ord-9cf732915bd94a6ebcbae7fec1c1460f
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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