Potassium Hydroxide → HCID 136009517, compound

HRID 1969872Notes

Reaction equation

HRID 1969872 reaction equation
[CH2:1]([C@H:3]1[C@@H:7]([C:8]2[N:12]3[C:13]4[CH:19]=[CH:18][NH:17][C:14]=4[N:15]=[CH:16][C:11]3=[N:10][N:9]=2)[CH2:6][C@@H:5]([NH:20][S:21]([CH:24]2[CH2:26][CH2:25]2)(=[O:23])=[O:22])[CH2:4]1)[CH3:2].[OH-].[K+].S([C:39]#[N:40])(C1C=CC(C)=CC=1)(=O)=O>CN(C=O)C>[C:39]([N:20]([C@@H:5]1[CH2:6][C@H:7]([C:8]2[N:12]3[C:13]4[CH:19]=[CH:18][NH:17][C:14]=4[N:15]=[CH:16][C:11]3=[N:10][N:9]=2)[C@H:3]([CH2:1][CH3:2])[CH2:4]1)[S:21]([CH:24]1[CH2:26][CH2:25]1)(=[O:23])=[O:22])#[N:40]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 87946p-Toluenesulphonyl cyanideHCID 135936828HCID 135936828, compound

Product 1

HCID 136009517HCID 136009517, compoundYield 5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the solution of N-((1S,3R,4S)-3-ethyl-4-(6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl)cyclopropanesulfonamide (0.05 g, 0.134 mmol, WO2009152133) in DMF (4 mL), KOH (0.022 g, 0.401 mmol) was added and the mixture was stirred at rt for about 5 min. Tosyl cyanide (0.024 g, 0.134 mmol) was added and stirring was continued for about 2 h. The solvent was removed under reduced pressure and the residue purified by preparative HPLC (Table 1, Method q) to yield N-cyano-N-((1S,3R,4S)-3-ethyl-4-(6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl)cyclopropanesulfonamide (0.0025 g, 5%) as an off-white solid: LC/MS (Table 1, Method a) Rt=1.84 min; MS m/z: 400 (M+H)+.

Workup

  1. stirringstirring
  2. waitwas continued for about 2 h
  3. customThe solvent was removed under reduced pressure
  4. customthe residue purified by preparative HPLC (Table 1, Method q)

Sources & evidence

ORD record
ord-952c808b6be94bf4b0ece3fd0c6d8164
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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