1H-Imidazole-1-propanamine → HCID 136364219, compound

HRID 1385540Notes

Reaction equation

HRID 1385540 reaction equation
Cl[C:2]1[N:3]=[C:4]([OH:19])[C:5]2[N:6]=[CH:7][N:8]([C:17]=2[N:18]=1)[C@@H:9]1[O:16][C@H:13]([CH2:14][OH:15])[C@@H:11]([OH:12])[CH2:10]1.[NH2:20][CH2:21][CH2:22][CH2:23][N:24]1[CH:28]=[CH:27][N:26]=[CH:25]1>COCCO>[N:24]1([CH2:23][CH2:22][CH2:21][NH:20][C:2]2[NH:3][C:4](=[O:19])[C:5]3[N:6]=[CH:7][N:8]([C:17]=3[N:18]=2)[C@@H:9]2[O:16][C@H:13]([CH2:14][OH:15])[C@@H:11]([OH:12])[CH2:10]2)[CH:28]=[CH:27][N:26]=[CH:25]1

Participants

4

Reactant 2

HCID 787361H-Imidazole-1-propanamineHCID 178521063HCID 178521063, compound

Product 1

HCID 136364219HCID 136364219, compound

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of the nucleoside 102 (10.31 g, 36 mmol) and 1-(3-amino-propyl) imidazol (9 g, 72 mmole) in 2-methoxyethanol (60 ml) was heated in a steel bomb at 120° C. (oil bath) for 24 hrs. The bomb was cooled to 0° C., opened carefully and the precipitated solid was filtered. The solid was washed with methanol (50 ml) and acetone (50 ml), and dried over sodium hydroxide to give 9 g (67%) of pure 103. A small amount was recrystallized from DMF for analytical purposes. mp 245-47°.

Workup

  1. filtrationthe precipitated solid was filtered
  2. washThe solid was washed with methanol (50 ml) and acetone (50 ml)
  3. dry with materialdried over sodium hydroxide
  4. customto give 9 g (67%) of pure 103
  5. customA small amount was recrystallized from DMF for analytical purposes

Sources & evidence

ORD record
ord-95140224c8854bbfacaa53c350e4556c
Source dataset
uspto-grants-2001_07
Patent number
US06262241B1

Reaction notes

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