1,3-Propanediamine → HCID 178465186, compound

HRID 582546Notes

Reaction equation

HRID 582546 reaction equation
Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[O:17][C@H:16]([C:18]([NH:20][CH2:21][CH3:22])=[O:19])[C@@H:14]([OH:15])[C@H:12]2[OH:13])=[C:4]([NH:23][CH2:24][CH:25]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:3]=1.[NH2:38][CH2:39][CH2:40][CH2:41][NH2:42].Cl.[N:44]1(C(N)=N)[CH:48]=CC=[N:45]1.N1C=CN=C1>CS(C)=O.CO>[NH2:45][N:44]=[CH:48][NH:38][CH2:39][CH2:40][CH2:41][NH:42][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[O:17][C@H:16]([C:18]([NH:20][CH2:21][CH3:22])=[O:19])[C@@H:14]([OH:15])[C@H:12]2[OH:13])=[C:4]([NH:23][CH2:24][CH:25]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:3]=1

Participants

7

Reactant 4

HCID 4281,3-PropanediamineHCID 795ImidazoleHCID 2734672Pyrazole-1-carboxamidine monohydrochloride2×HCID 86647542HCID 86647542, compound

Product 1

HCID 178465186HCID 178465186, compoundYield 56.6%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent

Procedure

A solution of 1-[2-chloro6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl]-1-deoxy-N-ethyl-β-D-ribofuranuronamide (0.310, 0.592 mmol) in dimethylsulphoxide (2 ml) was heated with 1,3-diaminopropane (0.542 g, 7.31 mmol) at 120° for 24h. The cooled mixture was partitioned between ethyl acetate (50 ml) and water (50 ml) and the aqueous phase was separated and extracted with ethyl acetate (20 ml). The combined ethyl acetate solution was washed with water (20 ml), dried (MgSO4) and evaporated to leave a froth (0.302 g). This froth (0.3 g) was dissolved in 50% aqueous methanol (20 ml) and the solution was heated at reflux with pyrazole-1-carboxamidine hydrochloride (0.099 g, 0.675 mmol) and imidazole (0.05 g, 0.734 mmol) for 18h. More pyrazole-1-carboxamidine hydrochloride (0.099 g, 0.675 mmol) was added and heating was continued for a further 24h. The mixture was evaporated to leave a solid which was purified by preparative HPLC (20-60% acetonitrile) to give the title compound (0.202 g) as a solid from ether. The product had MH+ =603, nmr(δ,DMSO-d6) includes 1.02(t,3H), 1.7-1.9(m,2H), 3.05-3.25(m,4H), 3.3-3.5(m,2H), 4.15-4.25(m,1H), 4.8(s,1H), 4.5-4.7(m,2H), 5.85(d,1H), 7.15-7.4(m,10H), 7.5-7.65(m,1H), 8.12(s,1H), 8.1-8.25(m,1H).

Workup

  1. customThe cooled mixture was partitioned between ethyl acetate (50 ml) and water (50 ml)
  2. customthe aqueous phase was separated
  3. extractionextracted with ethyl acetate (20 ml)
  4. washThe combined ethyl acetate solution was washed with water (20 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customto leave a froth (0.302 g)
  8. temperaturethe solution was heated
  9. temperatureheating
  10. customThe mixture was evaporated
  11. customto leave a solid which
  12. customwas purified by preparative HPLC (20-60% acetonitrile)

Sources & evidence

ORD record
ord-4a89a9d684924a389116ecad17f1f1c8
Source dataset
uspto-grants-1999_07
Patent number
US05925624

Reaction notes

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