1-Heptanamine → HCID 53793581, compound

HRID 1029719Notes

Reaction equation

HRID 1029719 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].[CH2:33](N)[CH2:34][CH2:35][CH2:36][CH2:37]CC.C(=O)(O)[O-].[Na+]>O1CCCC1.O.C(O)(=O)C>[CH2:32]([NH:28][C:21](=[O:22])[O:14][C:10]1[CH:9]=[C:8]2[C:13](=[CH:12][CH:11]=1)[N:5]([N:4]([CH2:1][CH2:2][CH3:3])[C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1)[CH:6]=[CH:7]2)[CH2:31][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]

Participants

8

Reactant 4

HCID 81271-HeptanamineHCID 682631,1'-CarbonyldiimidazoleHCID 516892Sodium BicarbonateHCID 18960815HCID 18960815, compound

Product 1

HCID 53793581HCID 53793581, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolvent2×HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To 1-(propyl-4-pyridinylamino)-1H-indol-5-ol (2.5 g) in 50 ml tetrahydrofuran was added 1,1'-carbonyldiimidazole (1.83 g) portionwise, and the reaction was allowed to proceed for 24 hours. To this mixture was added glacial acetic acid (2.15 ml) followed by a solution of heptylamine (1.45 ml) in tetrahydrofuran which had been treated with 0.56 ml of acetic acid. The reaction mixture was then stirred for 21 hours. The mixture was diluted with water, basified with sodium bicarbonate, 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/dichloromethane on a silica gel column via HPLC. The desired fractions were concentrated to yield an oil (4.5 g), which was eluted with 5% methanol/dichloromethane on a silica gel column via HPLC. The desired fractions were concentrated to yield an oil (2.8 g). This material was dissolved in 50 ml of pentane/ether (1:1) and the solution was concentrated to 15 ml, whereupon crystals precipitated out of the solution. These were collected to yield a solid (1.0 g), m.p. 83°-85° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried (sat. NaCl
  4. filtrationAfter filtration
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-52d093b1bd684cf1bc1976028c0d2717
Source dataset
uspto-grants-1992_04
Patent number
US05102891

Reaction notes

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