HCID 86647542, compound → HCID 178465188, compound

HRID 582543Notes

Reaction equation

HRID 582543 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.[C@H:38]1([NH2:45])[CH2:43][CH2:42][C@H:41]([NH2:44])[CH2:40][CH2:39]1>CS(C)=O.C(OCC)(=O)C.O.C(O)C>[NH3:3].[NH2:44][C@H:41]1[CH2:42][CH2:43][C@H:38]([NH:45][C:2]2[N:10]=[C:9]3[C:5]([N:6]=[CH:7][N:8]3[C@@H:11]3[O:17][C@H:16]([C:18]([NH:20][CH2:21][CH3:22])=[O:19])[C@@H:14]([OH:15])[C@H:12]3[OH:13])=[C:4]([NH:23][CH2:24][CH:25]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[N:3]=2)[CH2:39][CH2:40]1

Participants

8

Reactant 2

HCID 86647542HCID 86647542, compoundHCID 178511674HCID 178511674, compound

Product 2

HCID 222AmmoniaHCID 178465188HCID 178465188, compoundYield 165.6%

Reagents, catalysts & solvents 4

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-[2-chloro-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl]-1-deoxy-N-ethyl-β-D-ribofuranuronamide (18.0 g,0.0344 mole) in dimethylsulphoxide (100 ml) was heated at 120° under nitrogen with trans-cyclohexane-1,4-diamine (29.5 g, 0.258 mole) for 48h. The cooled mixture was diluted with ethyl acetate (1 l) and water (500 ml). The aqueous phase, which contained a considerable amount of oil, was separated from the ethyl acetate. The water was decanted from the oil and then extracted with ethyl acetate (100 ml) and the ethyl acetate solutions were combined, dried (MgSO4) and evaporated to leave a froth (9.2 g). The oil was dissolved in ethanol (500 ml) and the solution was evaporated to leave a solid which was dried in vacuo. The solid was leached with ethanol (3×200 ml) and the filtered solution was evaporated in vacuo to leave a froth (11.1 g). The two product fractions were combined and purified by column chromatography on flash silica eluted with dichloromethane:ethanol:0.88 ammonia (30:8:1) to give the title compound (17.11 g). The product had nmr(δ,CDCl3) including 1.1(t,3H), 1.1-1.35(m,4H),1.75-1.95(m,2H), 1.95-2.2(m,2H), 3.05-3.25(m,1H), 3.2-3.5(m,1H), 4.5-4.8(m,1H), 4.1-4.3(m,2H), 4.35(t,1H), 4.5(d,1H), 4.67(d,1H), 4.8(m,2H), 5.7-5.9(m,1H), 5.8(d,1H), 7.1-7.4(m,10H), 7.47(s,1H).

Workup

  1. customwas separated from the ethyl acetate
  2. customThe water was decanted from the oil
  3. extractionextracted with ethyl acetate (100 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customto leave a froth (9.2 g)
  7. customthe solution was evaporated
  8. customto leave a solid which
  9. customwas dried in vacuo
  10. customthe filtered solution was evaporated in vacuo
  11. customto leave a froth (11.1 g)
  12. custompurified by column chromatography on flash silica
  13. washeluted with dichloromethane

Sources & evidence

ORD record
ord-d392d71817bd4515b51b22fa9fbc695a
Source dataset
uspto-grants-1999_07
Patent number
US05925624

Reaction notes

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