Sodium Carbonate → 1,1-dimethylethyl (1-{[3,8-difluoro-4-hydroxy-7-oxo-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-4-yl]methyl}-4-piperidinyl)carbamate

HRID 15139

反応式

HRID 15139 の反応式
CC1C=CC(S(O[CH2:12][C:13]2([OH:28])[C:17]3=[C:18]([F:27])[CH:19]=[N:20][C:21]4[CH:22]=[C:23]([F:26])[C:24](=[O:25])[N:15]([C:16]=43)[CH2:14]2)(=O)=O)=CC=1.C(=O)([O-])[O-].[Na+].[Na+].[NH:35]1[CH2:40][CH2:39][CH:38]([NH:41][C:42](=[O:48])[O:43][C:44]([CH3:47])([CH3:46])[CH3:45])[CH2:37][CH2:36]1>C(O)C>[F:27][C:18]1[CH:19]=[N:20][C:21]2[CH:22]=[C:23]([F:26])[C:24](=[O:25])[N:15]3[CH2:14][C:13]([CH2:12][N:35]4[CH2:36][CH2:37][CH:38]([NH:41][C:42](=[O:48])[O:43][C:44]([CH3:46])([CH3:45])[CH3:47])[CH2:39][CH2:40]4)([OH:28])[C:17]=1[C:16]=23

参加物

5

反応物 3

HCID 10340Sodium CarbonateHCID 7238334-(N-Boc-amino)piperidineHCID 86614148[3,8-difluoro-4-hydroxy-7-oxo-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-4-yl]methyl 4-methylbenzenesulfonate

生成物 1

HCID 866141491,1-dimethylethyl (1-{[3,8-difluoro-4-hydroxy-7-oxo-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-4-yl]methyl}-4-piperidinyl)carbamate

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of crude [3,8-difluoro-4-hydroxy-7-oxo-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-4-yl]methyl 4-methylbenzenesulfonate (1.2 g, 2.79 mmol) in ethanol (40 mL) was treated with sodium carbonate (889 mg, 8.38 mmol) and 1,1-dimethylethyl 4-piperidinylcarbamate (615 mg, 3.07 mmol). The reaction mixture was stirred at room temperature for 18 hours under argon, evaporated and treated with water (200 mL). The aqueous layer was extracted with a 10% solution of methanol in dichloromethane (3×200 mL) and the combined organic extracts dried over magnesium sulphate and evaporated. The residue was chromatographed eluting with a 0-10% gradient of methanol in dichloromethane affording a yellow solid (1.1 g, 91%).

後処理

  1. customevaporated
  2. additiontreated with water (200 mL)
  3. extractionThe aqueous layer was extracted with a 10% solution of methanol in dichloromethane (3×200 mL)
  4. dry with materialthe combined organic extracts dried over magnesium sulphate
  5. customevaporated
  6. customThe residue was chromatographed
  7. washeluting with a 0-10% gradient of methanol in dichloromethane affording a yellow solid (1.1 g, 91%)

出典と根拠

ORDレコード
ord-d95809ec6f3149dd8b3e41f27e2a93c7
出典データセット
uspto-grants-2010_06
特許番号
US07732460B2

関連ノート

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