Iodine → HCID 136468212, compound

HRID 1969648Notes

Reaction equation

HRID 1969648 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+].[I:29]I.[Cl-].[NH4+]>CN(C=O)C>[CH2:1]([C@H:3]1[C@@H:7]([C:8]2[N:12]3[C:13]4[C:19]([I:29])=[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]

Participants

6

Reactant 4

HCID 807IodineHCID 14797Potassium HydroxideHCID 25517Ammonium ChlorideHCID 135936828HCID 135936828, compound

Product 1

HCID 136468212HCID 136468212, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 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 (0.396 g, 1.06 mmol, prepared as detailed in WO2009152133) in DMF (20 mL) was added KOH (0.190 g, 3.38 mmol). The mixture was stirred at rt for 5 min. Iodine (0.268 g, 1.058 mmol) was added in small portions and the reaction mixture was stirred at rt for 30 min. The mixture was added dropwise into a saturated aqueous ammonium chloride (200 mL). The precipitate was collected by filtration, washed with water, and dried to give N-((1S,3R,4S)-3-ethyl-4-(8-iodo-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl)cyclopropanesulfonamide (0.494 g, 93%) as an off-white solid: LC/MS (Table 1, Method a) Rt=1.83 min; MS m/z 501 (M+H)+.

Workup

  1. stirringthe reaction mixture was stirred at rt for 30 min
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-c82b566efadb4e74ba8ebe248d44a604
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

Loading…