Acetic Acid → HCID 15616352, compound

HRID 2379152Notes

Reaction equation

HRID 2379152 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].[H-].[Na+].[CH:43]1(Br)[CH2:47][CH2:46][CH2:45][CH2:44]1.[OH-:49].[Na+].[C:51]([OH:54])(=[O:53])[CH3:52]>CN(C=O)C.C1COCC1.O>[C:28]([OH:40])(=[O:49])/[CH:29]=[CH:52]\[C:51]([OH:54])=[O:53].[CH:43]1([N:31]2[C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][C:37]=3[C:29]3[C:28](=[O:40])[N:27]([CH2:26][C:3]4[N:4]=[CH:5][NH:6][C:2]=4[CH3:1])[CH2:39][CH2:38][C:30]2=3)[CH2:47][CH2:46][CH2:45][CH2:44]1

Participants

9

Reactant 5

HCID 176Acetic AcidHCID 8728BromocyclopentaneHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 15616330HCID 15616330, compound

Product 1

HCID 15616352HCID 15616352, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2,3,4,5-tetrahydro-2-[[5-methyl-1-(triphenylmethyl)-1H-imidazol-4-yl]methyl]-1H-pyrido[4,3-b]indol-1-one (523 mg) in dry DMF (30 ml) was treated with sodium hydride (60% dispersion in oil; 46 mg) and stirred for 15 min. at 21° under nitrogen. Cyclopentyl bromide (298 mg) was then added dropwise, and the mixture was stirred for 1 h and then heated at reflux for 4 h. The solution was left at 21° for 2 days, and then treated with a mixture of acetic acid (7 ml), water (7 ml) and THF (8 ml). The resulting solution was heated at reflux for 4 h, then basified with 2N sodium hydroxide and extracted with dichloromethane (3×25 ml). The combined extracts were washed with water (2×50 ml), concentrated in vacuo and purified by FCC eluting with System A (100:8:1) to give the free base of the title compound (42 mg) as a solid. Maleate formation gave the title compound (38 mg), m.p. 180° (decomp.), t.l.c. (System A, 100:8:1) Rf 0.3.

Workup

  1. stirringthe mixture was stirred for 1 h
  2. temperatureheated
  3. temperatureat reflux for 4 h
  4. waitThe solution was left at 21° for 2 days
  5. temperatureThe resulting solution was heated
  6. temperatureat reflux for 4 h
  7. extractionextracted with dichloromethane (3×25 ml)
  8. washThe combined extracts were washed with water (2×50 ml)
  9. concentrationconcentrated in vacuo
  10. custompurified by FCC
  11. washeluting with System A (100:8:1)

Sources & evidence

ORD record
ord-102ac69049b94c51a6d011b6280136d4
Source dataset
uspto-grants-1994_11
Patent number
US05360800

Reaction notes

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