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Water → HCID 58382317, compound

HRID 1628026
Notes
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Reaction equation

HRID 1628026 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([C:24]2[C:25]([CH3:30])=[N:26][CH:27]=[CH:28][CH:29]=2)[N:5]2[C:10]3[CH:11]=[CH:12][N:13]([S:14]([C:17]4[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=4)(=[O:16])=[O:15])[C:9]=3[N:8]=[CH:7][C:6]=12.[OH2:31]>O1CCOCC1>[Br:1][C:2]1[N:3]=[C:4]([C:24]2[C:25]([CH:30]=[O:31])=[N:26][CH:27]=[CH:28][CH:29]=2)[N:5]2[C:10]3[CH:11]=[CH:12][N:13]([S:14]([C:17]4[CH:18]=[CH:19][C:20]([CH3:21])=[CH:22][CH:23]=4)(=[O:16])=[O:15])[C:9]=3[N:8]=[CH:7][C:6]=12
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 962WaterHCID 583824443-bromo-1-(2-methylpyridin-3-yl)-6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine

Product 1

HCID 58382317HCID 58382317, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
105 °C

Procedure

The 3-bromo-1-(2-methylpyridin-3-yl)-6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine (0.500 g, 1.03 mmol, prepared using J.1 from Example #2, Step B with 2-methylnicotinic acid, L.2 with POCl3 and AB) in 1,4-dioxane (20 mL) was treated with SeO2 (0.210 g, 1.89 mmol) then the mixture was heated at about 105° C. for about 1 h. The mixture was cooled to rt then water (0.6 mL) was added. The mixture was heated to reflux for about 3 days. The mixture was cooled to rt then concentrated in vacuo. The material was purified using a 10 g silica column eluting with EtOAc. The impure fractions were combined and concentrated then the material was purified using a 10 g silica column eluting with EtOAc. The materials were combined to give 3-(3-bromo-6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)picolinaldehyde (0.355 g, 69%): LC/MS (Table 2, Method b) Rt=3.53 min; MS m/z 480 (M+H)+.

Workup

  1. temperatureThe mixture was cooled to rt
  2. temperatureThe mixture was heated
  3. temperatureto reflux for about 3 days
  4. temperatureThe mixture was cooled to rt
  5. concentrationthen concentrated in vacuo
  6. customThe material was purified
  7. washeluting with EtOAc
  8. concentrationconcentrated
  9. customthe material was purified
  10. washeluting with EtOAc

Sources & evidence

ORD record
ord-f119cdc2401d43ee80f4428235d57f59
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08785639B2

Reaction notes

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