Sodium Chloride → HCID 178428182, compound

HRID 1607169Notes

Reaction equation

HRID 1607169 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1([CH3:27])[C:25]2[C:11](=[CH:12][C:13]3[NH:17][C:16]([C:18]4[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=4)=[N:15][C:14]=3[CH:24]=2)[NH:10][C:9]1=O.[Cl-].[Na+]>O1CCCC1>[CH3:7][C:8]1([CH3:27])[C:25]2[C:11](=[CH:12][C:13]3[NH:17][C:16]([C:18]4[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=4)=[N:15][C:14]=3[CH:24]=2)[NH:10][CH2:9]1

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 21226445Aluminium lithium hydrideHCID 178429212HCID 178429212, compound

Product 1

HCID 178428182HCID 178428182, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 3.5 g. lithium aluminium hydride in 100 ml. tetrahydrofuran is added dropwise at ambient temperature a solution of 5.3 g. (19 mmole) 7,7-dimethyl-6,7-dihydro-2-(pyridin-4-yl)-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one. The reaction mixture is heated to reflux for 6 hours, decomposed with an aqueous solution of sodium chloride, extracted with dichloromethane and methanol, dried, evaporated and chromatographed on silica gel, 1.9 g. (38% of theory) of the title compound being eluted; m.p. 147°-149° C.

Workup

  1. additionTo a suspension of 3.5 g
  2. temperatureThe reaction mixture is heated
  3. temperatureto reflux for 6 hours
  4. extractionextracted with dichloromethane and methanol
  5. customdried
  6. customevaporated
  7. customchromatographed on silica gel, 1.9 g
  8. wash(38% of theory) of the title compound being eluted

Sources & evidence

ORD record
ord-64fc92bbb05d4199bee4e4ac6729aed7
Source dataset
uspto-grants-1989_09
Patent number
US04863945

Reaction notes

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