Iodine → 1-((1S,3R)-3-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl)-1H-pyrrole-3-carbonitrile

HRID 1969510Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1969510
[S:1]([N:11]1[C:15]2[N:16]=[CH:17][C:18]3[N:19]([C:20]([C@@H:23]4[CH2:27][CH2:26][C@H:25]([N:28]5[CH:32]=[CH:31][C:30]([CH:33]=O)=[CH:29]5)[CH2:24]4)=[N:21][N:22]=3)[C:14]=2[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].II.[NH4+:37].[OH-]>C1COCC1.[O-]S([O-])=O.[Na+].[Na+].CCOC(C)=O>[S:1]([N:11]1[C:15]2[N:16]=[CH:17][C:18]3[N:19]([C:20]([C@@H:23]4[CH2:27][CH2:26][C@H:25]([N:28]5[CH:32]=[CH:31][C:30]([C:33]#[N:37])=[CH:29]5)[CH2:24]4)=[N:21][N:22]=3)[C:14]=2[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2]

Komponenten

7

Edukt 3

HCID 807IodineHCID 14923Ammonium HydroxideHCID 866604291-((1S,3R)-3-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl)-1H-pyrrole-3-carbaldehyde

Produkt 1

HCID 679985851-((1S,3R)-3-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl)-1H-pyrrole-3-carbonitrileAusbeute 101 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 24437Sodium SulfiteLösungsmittel

Versuchsvorschrift

To a solution of 1-((1S,3R)-3-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl)-1H-pyrrole-3-carbaldehyde (0.050 g, 0.105 mmol) in THF (2 mL) was added iodine (0.083 g, 0.327 mmol) and aqueous NH4OH (28-30% w/v, 0.733 mL, 5.27 mmol). The reaction mixture was stirred at ambient temperature for about 24 h. The reaction mixture was diluted with saturated aqueous Na2SO3 (30 mL) and EtOAc (30 mL). The layers were partitioned and the organic layer was dried over anhydrous MgSO4, filtered, and the solvent was removed under reduced pressure to give 1-((1S,3R)-3-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl)-1H-pyrrole-3-carbonitrile (0.05 g, 100%): LC/MS (Table 1, Method a) Rt=2.33 min; MS m/z: 472 (M+H)+.

Aufarbeitung

  1. customThe layers were partitioned
  2. dry with materialthe organic layer was dried over anhydrous MgSO4
  3. filtrationfiltered
  4. customthe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-7b982bc9d2fe446eb1c1edb8730f7b86
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08426411B2

Notizen zur Reaktion

Wird geladen…