Iodine → 1-((1S,3R)-3-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl)-1H-pyrrole-3-carbonitrile

HRID 1969510Notes

Reaction equation

HRID 1969510 reaction equation
[S:1]([N:11]1[C:15]2[N:16]=[CH:17][C:18]3[N:19]([C:20]([C@@H:23]4[CH2:27][CH2:26][C@H:25]([N:28]5[CH:32]=[CH:31][C:30]([CH:33]=O)=[CH:29]5)[CH2:24]4)=[N:21][N:22]=3)[C:14]=2[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].II.[NH4+:37].[OH-]>C1COCC1.[O-]S([O-])=O.[Na+].[Na+].CCOC(C)=O>[S:1]([N:11]1[C:15]2[N:16]=[CH:17][C:18]3[N:19]([C:20]([C@@H:23]4[CH2:27][CH2:26][C@H:25]([N:28]5[CH:32]=[CH:31][C:30]([C:33]#[N:37])=[CH:29]5)[CH2:24]4)=[N:21][N:22]=3)[C:14]=2[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2]

Participants

7

Reactant 3

HCID 807IodineHCID 14923Ammonium HydroxideHCID 866604291-((1S,3R)-3-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl)-1H-pyrrole-3-carbaldehyde

Product 1

HCID 679985851-((1S,3R)-3-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl)-1H-pyrrole-3-carbonitrileYield 101%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 24437Sodium SulfiteSolvent

Procedure

To a solution of 1-((1S,3R)-3-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl)-1H-pyrrole-3-carbaldehyde (0.050 g, 0.105 mmol) in THF (2 mL) was added iodine (0.083 g, 0.327 mmol) and aqueous NH4OH (28-30% w/v, 0.733 mL, 5.27 mmol). The reaction mixture was stirred at ambient temperature for about 24 h. The reaction mixture was diluted with saturated aqueous Na2SO3 (30 mL) and EtOAc (30 mL). The layers were partitioned and the organic layer was dried over anhydrous MgSO4, filtered, and the solvent was removed under reduced pressure to give 1-((1S,3R)-3-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl)-1H-pyrrole-3-carbonitrile (0.05 g, 100%): LC/MS (Table 1, Method a) Rt=2.33 min; MS m/z: 472 (M+H)+.

Workup

  1. customThe layers were partitioned
  2. dry with materialthe organic layer was dried over anhydrous MgSO4
  3. filtrationfiltered
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-7b982bc9d2fe446eb1c1edb8730f7b86
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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