3-Chloropropanesulphonyl chloride → 3-chloro-N-((1S,3R)-3-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl)propane-1-sulfonamide

HRID 1969507Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1969507
Cl.[S:2]([N:12]1[C:16]2[N:17]=[CH:18][C:19]3[N:20]([C:21]([C@@H:24]4[CH2:28][CH2:27][C@H:26]([NH2:29])[CH2:25]4)=[N:22][N:23]=3)[C:15]=2[CH:14]=[CH:13]1)([C:5]1[CH:11]=[CH:10][C:8]([CH3:9])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[Cl:30][CH2:31][CH2:32][CH2:33][S:34](Cl)(=[O:36])=[O:35]>C(Cl)Cl.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[Cl:30][CH2:31][CH2:32][CH2:33][S:34]([NH:29][C@H:26]1[CH2:27][CH2:28][C@@H:24]([C:21]2[N:20]3[C:15]4[CH:14]=[CH:13][N:12]([S:2]([C:5]5[CH:11]=[CH:10][C:8]([CH3:9])=[CH:7][CH:6]=5)(=[O:4])=[O:3])[C:16]=4[N:17]=[CH:18][C:19]3=[N:23][N:22]=2)[CH2:25]1)(=[O:36])=[O:35]

Komponenten

5

Edukt 2

HCID 154103-Chloropropanesulphonyl chlorideHCID 69014326(1S,3R)-3-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentanamine hydrochloride

Produkt 1

HCID 679981583-chloro-N-((1S,3R)-3-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl)propane-1-sulfonamideAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 311Citric AcidLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a suspension of (1S,3R)-3-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentanamine hydrochloride (0.05 g, 0.11 mmol, prepared using E from Preparation #B.1 and HCl) and TEA (0.03 mL, 0.21 mmol) in DCM (5 mL) at about 0° C. was added 3-chloropropane-1-sulfonyl chloride (0.02 g, 0.11 mmol) dropwise. The reaction mixture was stirred at about 0° C. for about 1.5 h. The reaction mixture was diluted with 5% aqueous citric acid (10 mL), and the layers were separated. The organic layer was washed with saturated aqueous NaHCO3 (10 mL), water (10 mL), brine (10 mL), dried over anhydrous MgSO4, filtered, and concd under reduced pressure to give 3-chloro-N-((1S,3R)-3-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl)propane-1-sulfonamide (0.052 g, 91%) as a brown residue: LC/MS (Table 1, Method a) Rt=2.18 min; MS m/z: 537 (M+H)+.

Aufarbeitung

  1. customthe layers were separated
  2. washThe organic layer was washed with saturated aqueous NaHCO3 (10 mL), water (10 mL), brine (10 mL)
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-cd26e9e9294d4c33b0a386cabfbb2ee0
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08426411B2

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