Acetic Acid → HCID 54021051, compound

HRID 1029723Notes

Reaction equation

HRID 1029723 reaction equation
[CH2:1]([N:4]([C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1)[N:5]1[C:13]2[C:8](=[CH:9][C:10]([OH:14])=[CH:11][CH:12]=2)[CH:7]=[CH:6]1)[CH2:2][CH3:3].[C:21](N1C=CN=C1)([N:23]1C=CN=C1)=[O:22].C(O)(=O)C.[NH:37]1[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1>O1CCCC1>[N:37]1([NH:23][C:21](=[O:22])[O:14][C:10]2[CH:9]=[C:8]3[C:13](=[CH:12][CH:11]=2)[N:5]([N:4]([CH2:1][CH2:2][CH3:3])[C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)[CH:6]=[CH:7]3)[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 682631,1'-CarbonyldiimidazoleHCID 18960815HCID 18960815, compound

Product 1

HCID 54021051HCID 54021051, compoundYield 125%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1-(propyl-4-pyridinylamino)-1H-indol-5-ol (2.5 g) in 60 ml of tetrahydrofuran was added 1,1'-carbonyldiimidazole (1.83 g) and this mixture was stirred for 24 hours. Then 4.5 ml of glacial acetic acid was added to the reaction mixture followed by piperidine (0.95 g) in 10 ml of tetrahydrofuran. This mixture was then stirred for 24 hours, quenched with water and basified with saturated sodium carbonate solution and extracted with ethyl acetate. The organic layer was washed with water and dried (sat. NaCl, anhy. MgSO4). After filtration, the solvent was evaporated to yield an oil (4.6 g), which was eluted with 5% methanol in dichloromethane on a silica gel column via HPLC. The desired fractions were concentrated to yield an oil (3.65 g).

Workup

  1. stirringThis mixture was then stirred for 24 hours
  2. customquenched with water and basified with saturated sodium carbonate solution
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried (sat. NaCl
  6. filtrationAfter filtration
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-a269492d75314356aca7465e393d8243
Source dataset
uspto-grants-1992_04
Patent number
US05102891

Reaction notes

Loading…