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 1969507Notes

Reaction equation

HRID 1969507 reaction equation
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]

Participants

5

Reactant 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

Product 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-sulfonamideYield 91%

Reagents, catalysts & solvents 2

HCID 311Citric AcidSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-cd26e9e9294d4c33b0a386cabfbb2ee0
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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