Cyclohexylamine → HCID 10022873, compound

HRID 1260155Notes

Reaction equation

HRID 1260155 reaction equation
[Cl:1][C:2]1[N:19]=[C:18]2[C:5](=[N:6][CH2:7][N:8]2[C@@H:9]2[O:17][C@H:14]([CH2:15][OH:16])[C@@H:12]([OH:13])[C@H:10]2[OH:11])[C:4](Cl)([NH2:20])[N:3]=1.[CH:22]1(N)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1>C(O)C>[Cl:1][C:2]1[N:3]=[C:4]([NH:20][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)[C:5]2[N:6]=[CH:7][N:8]([C:18]=2[N:19]=1)[C@@H:9]1[O:17][C@H:14]([CH2:15][OH:16])[C@@H:12]([OH:13])[C@H:10]1[OH:11]

Participants

4

Reactant 2

HCID 7965CyclohexylamineHCID 66601565HCID 66601565, compound

Product 1

HCID 10022873HCID 10022873, compoundYield 229.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2,6-dichloroadenosine (1.0 g) and cyclohexylamine (0.926 g) in ethanol (30 ml) was heated at reflux for 6 hours then cooled to room temperature. The mixture was concentrated under vacuo. The residue was purified on the silica gel column using MeOH—CH2Cl2 (1:6 to 1:5). The combined fractions were concentrated and dried under vacuum to provide 2-chloro-N6-cyclohexyladenosine as a white solid (2.600 g). 1H NMR (DMSO-D6): δ 1.12-1.21 (m, 2H), 1.33-1.43 (m, 3H), 1.63-1.86 (m, 6H), 3.57-3.62 (m, 1H), 3.66-3.69 (m, 1H), 3.97 (d, J=3 Hz, 1H), 4.16 (d, J=3.3 Hz, 1H), 4.54 (d, J=5.4 Hz, 1H), 5.08-5.11 (m, 1H), 5.24 (d, J=4.8 Hz, 1H), 5.51 (d, J=5.7 Hz, 1H), 5.85 (d, J=5.7 Hz, 1H), 8.26 (d, J=8.4 Hz, 1H), 8.41 (s, 1H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 6 hours
  3. concentrationThe mixture was concentrated under vacuo
  4. customThe residue was purified on the silica gel column
  5. concentrationThe combined fractions were concentrated
  6. customdried under vacuum

Sources & evidence

ORD record
ord-1d6a6792beb943d1a87f154d10274103
Source dataset
uspto-grants-2013_06
Patent number
US08470800B2

Reaction notes

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