Acetic Acid → HCID 54516575, compound

HRID 1029721Notes

Reaction equation

HRID 1029721 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]([N:28]1[CH:32]=[CH:31]N=C1)(N1C=CN=C1)=[O:22].C(O)(=O)C.[Cl:37][C:38]1[CH:43]=[CH:42]C(CN)=[CH:40][CH:39]=1>O1CCCC1>[Cl:37][C:38]1[CH:43]=[CH:42][C:31]([CH2:32][NH:28][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)=[CH:40][CH:39]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 660364-ChlorobenzylamineHCID 682631,1'-CarbonyldiimidazoleHCID 18960815HCID 18960815, compound

Product 1

HCID 54516575HCID 54516575, compoundYield 95.9%

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 4-chlorophenylmethylamine (1.5 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 (3.9 g), which was eluted with 5% methanol in dichloromethane on a silica gel column via HPLC. The desired fractions were concentrated to yield a solid (3.05 g), m.p. 149°-151° C.

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-5ed2f671beae4ebd89c6c6c960d41077
Source dataset
uspto-grants-1992_04
Patent number
US05102891

Reaction notes

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