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

반응식

HRID 527923 반응식
[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

참가 물질

8

반응물 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

생성물 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-amine수율 33%

시약·촉매·용매 3

HCID 23925Iron촉매HCID 702Ethanol용매HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-fd5238fc5b804296bb3e0cf629c60fe6
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346810B2

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