1-Heptanamine → HCID 54427198, compound

HRID 1029734Notes

Reaction equation

HRID 1029734 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([OH:11])[CH:9]=2)[N:4]([N:12]([CH2:19][CH2:20][CH3:21])[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)[CH:3]=1.[C:22]([N:29]1[CH:33]=[CH:32]N=C1)(N1C=CN=C1)=[O:23].[CH2:34](N)[CH2:35][CH2:36][CH2:37][CH2:38]CC.C(=O)(O)[O-].[Na+]>C1COCC1.C(O)(=O)C>[CH2:33]([NH:29][C:22](=[O:23])[O:11][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[N:4]([N:12]([CH2:19][CH2:20][CH3:21])[C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1)[CH:3]=[C:2]2[CH3:1])[CH2:32][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]

Participants

7

Reactant 4

HCID 81271-Heptanamine2×HCID 682631,1'-CarbonyldiimidazoleHCID 516892Sodium BicarbonateHCID 190723493-Methyl-1-[propyl(pyridin-4-yl)amino]-1H-indol-5-ol

Product 1

HCID 54427198HCID 54427198, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent3×HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution consisting of 3-methyl-1-(propyl-4-pyridinylamino)-1H-indol-5-ol (2.23 g) and tetrahydrofuran (53 ml) was added 1,1'-carbonyldiimidazole (2.57 g) at room temperature with stirring under nitrogen. Stirring was continued for 96 hours, at which time acetic acid (1.54 ml) was added. To the resulting reaction mixture was added a solution consisting of heptyl amine (1.76 ml), acetic acid (0.71 ml) and THF (5 ml). After stirring for 24 hours, an additional solution of heptyl amine (1.17 ml), acetic acid (0.48 ml) and THF (5 ml) was added and stirring continued for 3 hours. The reaction mixture was poured into a dilute aqueous sodium bicarbonate solution and the product extracted with ether (3x). The combined organic layer was washed with brine and dried (MgSO4). Filtration, concentration and purification via flash column chromatography (silica gel, 2% Et3N/ether) afforded 1.60 g of the desired carbamate after recrystallization from ether/pentane, m.p. 102°-104° C.

Workup

  1. stirringStirring
  2. additionwas added
  3. customTo the resulting reaction mixture
  4. additionwas added a solution
  5. stirringAfter stirring for 24 hours
  6. stirringstirring
  7. extractionthe product extracted with ether (3x)
  8. washThe combined organic layer was washed with brine
  9. dry with materialdried (MgSO4)
  10. filtrationFiltration, concentration and purification via flash column chromatography (silica gel, 2% Et3N/ether)

Sources & evidence

ORD record
ord-632b7a7858044aaeae947375b529172b
Source dataset
uspto-grants-1992_04
Patent number
US05102891

Reaction notes

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