Sodium Chloride → 7-chloro-6-(((1-(2-(2-oxo-1,8-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)amino)methyl)-2H-pyrido(3,2-b)(1,4)thiazin-3(4H)-one hydrochloride

HRID 385631

反応式

HRID 385631 の反応式
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][N:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][N:18]=3)[CH:13]=[CH:12][C:11]2=[O:20])[CH2:4][CH2:3]1.[Cl:21][C:22]1[C:31]([CH:32]=O)=[N:30][C:29]2[NH:28][C:27](=[O:34])[CH2:26][S:25][C:24]=2[CH:23]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+].[Cl-].[Na+]>ClCCl.C(Cl)(Cl)Cl.O.C(O)(=O)C>[ClH:21].[Cl:21][C:22]1[C:31]([CH2:32][NH:1][CH:2]2[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][N:10]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][N:18]=4)[CH:13]=[CH:12][C:11]3=[O:20])[CH2:4][CH2:3]2)=[N:30][C:29]2[NH:28][C:27](=[O:34])[CH2:26][S:25][C:24]=2[CH:23]=1

参加物

10

反応物 5

HCID 5234Sodium ChlorideHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride2 回HCID 218735897-Chloro-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carbaldehydeHCID 578152591-(2-(4-aminopiperidin-1-yl)ethyl)-1,8-naphthyridin-2(1H)-one

生成物 1

HCID 248668727-chloro-6-(((1-(2-(2-oxo-1,8-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)amino)methyl)-2H-pyrido(3,2-b)(1,4)thiazin-3(4H)-one hydrochloride収率 109.2%

試薬・触媒・溶媒 4

HCID 176Acetic Acid溶媒3 回HCID 962Water溶媒HCID 6212Chloroform溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of 0.07 g of 1-(2-(4-aminopiperidin-1-yl)ethyl)-1,8-naphthyridin-2(1H)-one in 3 mL of dichloromethane, 57 mg of 7-chloro-3-oxo-3,4-dihydro-2H-pyrido(3,2-b)(1,4)thiazine-6-carbaldehyde and 14 μL of acetic acid were added, the mixture was stirred for 10 minutes, and then, 79 mg of sodium triacetoxyborohydride was added to the reaction mixture, and the mixture was reacted for 1 day. Thereto was further added 7 μL of acetic acid, the mixture was stirred for 35 minutes, and then, 7 μL of acetic acid and 26 mg of sodium triacetoxyborohydride was added thereto, and the mixture was reacted for 20 minutes. To the reaction mixture, water, a saturated aqueous sodium hydrogen carbonate solution, chloroform and sodium chloride were added, the organic layer was separated, and the aqueous layer was extracted with chloroform while salting out. The organic layer and the extract were combined, the resultant solution was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The resultant residue was dissolved in 5 mL of 6 mol/L hydrochloric acid, and the solvent was distilled off under reduced pressure. The resultant residue was purified by reverse silica gel column chromatography using an eluent of water to obtain 71 mg of 7-chloro-6-(((1-(2-(2-oxo-1,8-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)amino)methyl)-2H-pyrido(3,2-b)(1,4)thiazin-3(4H)-one hydrochloride as a light gray solid.

後処理

  1. customthe mixture was reacted for 1 day
  2. stirringthe mixture was stirred for 35 minutes
  3. customthe mixture was reacted for 20 minutes
  4. customthe organic layer was separated
  5. extractionthe aqueous layer was extracted with chloroform
  6. dry with materialthe resultant solution was dried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. dissolutionThe resultant residue was dissolved in 5 mL of 6 mol/L hydrochloric acid
  9. distillationthe solvent was distilled off under reduced pressure
  10. customThe resultant residue was purified by reverse silica gel column chromatography

出典と根拠

ORDレコード
ord-29f2acafca874fd2bc5011a049f6097a
出典データセット
uspto-grants-2013_02
特許番号
US08367831B2

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