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Dimethylamine, hydrochloride → 5-Chloro-1H-indole-2-carboxylic acid [1-benzyl-2-(4-methylamino-piperidin-1-yl)-2-oxo-ethyl]-amide

HRID 651092
ノート
印刷プレビュー

反応式

HRID 651092 の反応式
Cl.[CH3:2][NH:3]C.C([O-])(=O)C.[Na+].C([BH3-])#N.[Na+].[CH2:14]([CH:21]([NH:31][C:32]([C:34]1[NH:35][C:36]2[C:41]([CH:42]=1)=[CH:40][C:39]([Cl:43])=[CH:38][CH:37]=2)=[O:33])[C:22](=[O:30])[N:23]1[CH2:28][CH2:27][C:26](=O)[CH2:25][CH2:24]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CO>[CH2:14]([CH:21]([NH:31][C:32]([C:34]1[NH:35][C:36]2[C:41]([CH:42]=1)=[CH:40][C:39]([Cl:43])=[CH:38][CH:37]=2)=[O:33])[C:22]([N:23]1[CH2:28][CH2:27][CH:26]([NH:3][CH3:2])[CH2:25][CH2:24]1)=[O:30])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 10473Dimethylamine, hydrochlorideHCID 517045Sodium AcetateHCID 5003444Sodium cyanoborohydrideHCID 543267115-chloro-1H-indole-2-carboxylic acid [1-benzyl-2-oxo-2-(4-oxo-piperidin-1-yl)-ethyl]-amide

生成物 1

HCID 536941855-Chloro-1H-indole-2-carboxylic acid [1-benzyl-2-(4-methylamino-piperidin-1-yl)-2-oxo-ethyl]-amide収率 82%

試薬・触媒・溶媒

1
HCID 887Methanol溶媒

実験手順

Dimethylamine hydrochloride (1.1 mmol), sodium acetate (2.1 mmol), activated 3A molecular seives, and sodium cyanoborohydride (0.25 mmol) were added in this order to 5-chloro-1H-indole-2-carboxylic acid [1-benzyl-2-oxo-2-(4-oxo-piperidin-1-yl)-ethyl]-amide (0.21 mmol) in methanol (2 mL) at 0° C. After 18 hours, the mixture was concentrated, the residue taken up in ethyl acetate, the resulting solution washed with 2N NaOH and brine, dried with Na2SO4 and concentrated. The product was purified by chromatography on silica gel eluted with 1-8% ethanol in dichloromethane containing 0.5 % NH4OH followed by trituration with ether: Yield 82%; HPLC (60/40) 2.79 minutes (98%); PBMS 439/441 (MH+,100%);

後処理

  1. concentrationthe mixture was concentrated
  2. washthe resulting solution washed with 2N NaOH and brine
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated
  5. customThe product was purified by chromatography on silica gel
  6. washeluted with 1-8% ethanol in dichloromethane containing 0.5 % NH4OH
  7. customHPLC (60/40) 2.79 minutes (98%)

出典と根拠

ORDレコード
ord-d15ad9d772964351bc7fc3a062a3b88a
出典データセット
uspto-grants-2001_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06277877B1

反応ノート

読み込み中…

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