Ammonium Chloride → (R)-N-methyl-N-(1-(7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrolidin-3-yl)-1H-pyrazolo[3,4-c]pyridin-5-amine

HRID 527923

反応式

HRID 527923 の反応式
[CH3:1][N:2]([C@@H:13]1[CH2:17][CH2:16][N:15]([C:18]2[C:19]3[CH:26]=[CH:25][N:24]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[C:20]=3[N:21]=[CH:22][N:23]=2)[CH2:14]1)[C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([N+:10]([O-])=O)=[CH:5][N:4]=1.[NH4+].[Cl-].[N:37]([O-])=O.[Na+].N.O>C(O)C.O.[Fe]>[CH3:1][N:2]([C@@H:13]1[CH2:17][CH2:16][N:15]([C:18]2[C:19]3[CH:26]=[CH:25][N:24]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[C:20]=3[N:21]=[CH:22][N:23]=2)[CH2:14]1)[C:3]1[CH:8]=[C:7]2[CH:9]=[N:37][NH:10][C:6]2=[CH:5][N:4]=1

参加物

8

反応物 4

HCID 25517Ammonium ChlorideHCID 12896473Azane;hydrateHCID 23668193Sodium NitriteHCID 86692145(R)-N,4-dimethyl-5-nitro-N-(1-(7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrolidin-3-yl)pyridin-2-amine

生成物 1

HCID 86692146(R)-N-methyl-N-(1-(7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrolidin-3-yl)-1H-pyrazolo[3,4-c]pyridin-5-amine収率 33%

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

To a solution of (R)—N,4-dimethyl-5-nitro-N-(1-(7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrolidin-3-yl)pyridin-2-amine (0.248 mmol) in ethanol (20 mL) and water (5 mL), was added iron powder (0.752 mmol) and NH4Cl (1.495 mmol). The mixture was stirred at refluxing temperature for 2 hours, cooled, and filtered. The filtrate was concentrated, and dissolved in CH3COOH (1.5 mL) and water (2.5 mL). NaNO2 (0.304 mmol) was then slowly added, and the mixture was stirred at room temperature overnight, which was subsequently treated with NH3.H2O and extracted with EtOAc (3×20 mL). The combined extracts were concentrated and the residue was purified by column chromatography to give the title compound in 33.0% yield.

後処理

  1. temperatureat refluxing temperature for 2 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. dissolutiondissolved in CH3COOH (1.5 mL)
  6. stirringthe mixture was stirred at room temperature overnight
  7. extractionextracted with EtOAc (3×20 mL)
  8. concentrationThe combined extracts were concentrated
  9. customthe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-fd5238fc5b804296bb3e0cf629c60fe6
出典データセット
uspto-grants-2016_05
特許番号
US09346810B2

関連ノート

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