Sodium Bicarbonate → 1-(2-(4-((4-fluoro-3-methylbenzyl)amino)piperidin-1-yl)ethyl)-7-methoxy-1,5-naphthyridin-2(1H)-one hydrochloride

HRID 385658노트

반응식

HRID 385658 반응식
[ClH:1].[NH2:2][CH:3]1[CH2:8][CH2:7][N:6]([CH2:9][CH2:10][N:11]2[C:20]3[C:15](=[N:16][CH:17]=[C:18]([O:21][CH3:22])[CH:19]=3)[CH:14]=[CH:13][C:12]2=[O:23])[CH2:5][CH2:4]1.C([BH3-])#N.C([BH3-])#N.[Na+].[F:31][C:32]1[CH:39]=[CH:38][C:35]([CH:36]=O)=[CH:34][C:33]=1[CH3:40].C[O-].[Na+].CO.C([BH3-])#N.[Na+].C(=O)([O-])O.[Na+]>CO.C(OCC)(=O)C.C(O)(=O)C>[ClH:1].[F:31][C:32]1[CH:39]=[CH:38][C:35]([CH2:36][NH:2][CH:3]2[CH2:4][CH2:5][N:6]([CH2:9][CH2:10][N:11]3[C:20]4[C:15](=[N:16][CH:17]=[C:18]([O:21][CH3:22])[CH:19]=4)[CH:14]=[CH:13][C:12]3=[O:23])[CH2:7][CH2:8]2)=[CH:34][C:33]=1[CH3:40]

참가 물질

10

반응물 6

HCID 516892Sodium BicarbonateHCID 27348744-Fluoro-3-methylbenzaldehyde3회HCID 5003444Sodium cyanoborohydrideHCID 23694274Sodium methanolate methanolHCID 689270711-(2-(4-aminopiperidin-1-yl)ethyl)-7-methoxy-1,5-naphthyridin-2(1H)-one hydrochlorideHCID 131729803Sodium cyanoborohydride cyanoborohydride2회

생성물 1

HCID 689292391-(2-(4-((4-fluoro-3-methylbenzyl)amino)piperidin-1-yl)ethyl)-7-methoxy-1,5-naphthyridin-2(1H)-one hydrochloride

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 887Methanol용매HCID 8857Ethyl Acetate용매

실험 절차

To a suspension of 0.10 g of 1-(2-(4-aminopiperidin-1-yl)ethyl)-7-methoxy-1,5-naphthyridin-2(1H)-one hydrochloride in 4 mL of methanol, 31 mg of sodium cyanoborohydride cyanoborohydride, 44 μL of 4-fluoro-3-methylbenzaldehyde, 39 mg of a 28% sodium methoxide/methanol solution and 42 μL of acetic acid were added, and the mixture was stirred at room temperature for 1 hour 15 minutes. Thereto were added 44 μL of 4-fluoro-3-methylbenzaldehyde and 31 mg of sodium cyanoborohydride cyanoborohydride, and the mixture was stirred at the same temperature for 45 minutes. Thereto were further added 44 μL of 4-fluoro-3-methylbenzaldehyde and 31 mg of sodium cyanoborohydride, and the mixture was stirred at the same temperature for 30 minutes. A saturated aqueous sodium hydrogen carbonate solution and ethyl acetate were added thereto, and the organic layer was separated, washed with a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The resultant residue was purified by basic silica gel column chromatography using an eluent of chloroform:methanol=10:1. The resultant residue was dissolved in 2 mL of ethyl acetate, and thereto was added 1 mL of a 4.0 mol/L hydrogen chloride/ethyl acetate solution at room temperature. The solvent was distilled off under reduced pressure, ethyl acetate was added to the resultant residue and the solid was filtered off to obtain 54 mg of 1-(2-(4-((4-fluoro-3-methylbenzyl)amino)piperidin-1-yl)ethyl)-7-methoxy-1,5-naphthyridin-2(1H)-one hydrochloride as a light yellow solid.

후처리

  1. additionwere added
  2. stirringthe mixture was stirred at the same temperature for 45 minutes
  3. stirringthe mixture was stirred at the same temperature for 30 minutes
  4. customthe organic layer was separated
  5. washwashed with a saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe resultant residue was purified by basic silica gel column chromatography
  9. dissolutionThe resultant residue was dissolved in 2 mL of ethyl acetate
  10. additionwas added 1 mL of a 4.0 mol/L hydrogen chloride/ethyl acetate solution at room temperature
  11. distillationThe solvent was distilled off under reduced pressure, ethyl acetate
  12. additionwas added to the resultant residue
  13. filtrationthe solid was filtered off

출처 및 근거

ORD 기록
ord-5f0974c6b0b64fa782a3d92889967a33
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367831B2

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