2-Chloroethyl chlorosulfonylcarbamate → N-((1S,3R,4S)-3-ethyl-4-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl)-2-oxooxazolidine-3-sulfonamide

HRID 1969642Notes

Reaction equation

HRID 1969642 reaction equation
Cl[S:2]([NH:5][C:6](=[O:11])[O:7][CH2:8][CH2:9]Cl)(=[O:4])=[O:3].[CH2:12]([C@H:14]1[C@@H:18]([C:19]2[N:23]3[C:24]4[CH:30]=[CH:29][N:28]([S:31]([C:34]5[CH:40]=[CH:39][C:37]([CH3:38])=[CH:36][CH:35]=5)(=[O:33])=[O:32])[C:25]=4[N:26]=[CH:27][C:22]3=[N:21][N:20]=2)[CH2:17][C@@H:16]([NH2:41])[CH2:15]1)[CH3:13]>C(Cl)Cl>[CH2:12]([C@H:14]1[C@@H:18]([C:19]2[N:23]3[C:24]4[CH:30]=[CH:29][N:28]([S:31]([C:34]5[CH:35]=[CH:36][C:37]([CH3:38])=[CH:39][CH:40]=5)(=[O:33])=[O:32])[C:25]=4[N:26]=[CH:27][C:22]3=[N:21][N:20]=2)[CH2:17][C@@H:16]([NH:41][S:2]([N:5]2[CH2:9][CH2:8][O:7][C:6]2=[O:11])(=[O:4])=[O:3])[CH2:15]1)[CH3:13]

Participants

4

Reactant 2

HCID 131188122-Chloroethyl chlorosulfonylcarbamateHCID 58557840(1S,3R,4S)-3-ethyl-4-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentanamine

Product 1

HCID 67999507N-((1S,3R,4S)-3-ethyl-4-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl)-2-oxooxazolidine-3-sulfonamideYield 72.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-chloroethyl chlorosulfonylcarbamate (prepared as detailed in Bioorg. Med. Chem. Lett., 2006 16, 3367-3370; 0.052 g, 0.236 mmol) and (1S,3R,4S)-3-ethyl-4-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentanamine (0.100 g, 0.236 mmol, Example #8 Step M) in DCM (2.4 mL) was added TEA (0.098 mL, 0.71 mmol) and the reaction mixture was stirred at ambient temperature for about 1 h. The reaction mixture was concd under reduced pressure to give N-((1S,3R,4S)-3-ethyl-4-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl)-2-oxooxazolidine-3-sulfonamide (0.098 g, 65%) as a light brown solid: LC/MS (Table 1, Method a) Rt=2.18 min; MS m/z 574 (M+H)+.

Sources & evidence

ORD record
ord-307ce39334a2438da23dbc4a2876b501
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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