Acetone → HCID 15616350, compound

HRID 2379151Notes

Reaction equation

HRID 2379151 reaction equation
[CH3:1][C:2]1[N:6](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:5]=[N:4][C:3]=1[CH2:26][N:27]1[CH2:39][CH2:38][C:30]2[NH:31][C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][C:37]=3[C:29]=2[C:28]1=[O:40].[C:41](=[O:44])([O-:43])[O-].[K+].[K+].[CH2:47](Br)[C:48]#[CH:49].CC(C)=[O:53]>>[C:28]([OH:40])(=[O:53])/[CH:29]=[CH:37]\[C:41]([OH:43])=[O:44].[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[CH2:26][N:27]1[CH2:39][CH2:38][C:30]2[N:31]([CH2:49][C:48]#[CH:47])[C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][C:37]=3[C:29]=2[C:28]1=[O:40]

Participants

5

Reactant 4

HCID 180AcetoneHCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 15616330HCID 15616330, compound

Product 1

HCID 15616350HCID 15616350, compound

Procedure

A suspension of 2,3,4,5-tetrahydro-2-[[5-methyl-1-(triphenylmethyl)-1H-imidazol-4-yl]methyl]-1H-pyrido[4,3-b]indol-1-one (522 mg) and potassium carbonate (276 mg) in dry acetone (75 ml) was treated with propargyl bromide (1M solution in acetone; 2 ml) and the mixture was heated at reflux overnight. After cooling, excess acetone was removed in vacuo to give an oil which was partitioned between water (100 ml) and ethyl acetate (100 ml). The aqueous phase was washed with ethyl acetate (50 ml) and the combined organic extracts were concentrated in vacuo. Deprotection, work-up and purification gave the free base of the title compound (100 mg) as a solid. Maleate formation gave the title compound (89 mg), m.p. 202°-205°, t.l.c. (System A, 100:8:1) Rf 0.29.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux overnight
  3. temperatureAfter cooling
  4. customexcess acetone was removed in vacuo
  5. customto give an oil which
  6. customwas partitioned between water (100 ml) and ethyl acetate (100 ml)
  7. washThe aqueous phase was washed with ethyl acetate (50 ml)
  8. concentrationthe combined organic extracts were concentrated in vacuo
  9. customDeprotection, work-up and purification

Sources & evidence

ORD record
ord-ec2d215ffb0c4cf6a5211fac5b3b382f
Source dataset
uspto-grants-1994_11
Patent number
US05360800

Reaction notes

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