3-Pentanamine → HCID 86588182, compound

HRID 1839261Notes

Reaction equation

HRID 1839261 reaction equation
[C:1]([O:4][C@@H:5]1[C@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@@H:8]([C:14]2[CH:18]=[C:17]([CH2:19][CH3:20])[O:16][N:15]=2)[O:7][C@H:6]1[N:21]1[CH:29]=[N:28][C:27]2[C:22]1=[N:23][C:24]([Cl:31])=[N:25][C:26]=2Cl)(=[O:3])[CH3:2].C(N(C(C)C)CC)(C)C.[CH2:41]([CH:43]([NH2:46])[CH2:44][CH3:45])[CH3:42]>C(O)(C)C>[C:1]([O:4][C@@H:5]1[C@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@@H:8]([C:14]2[CH:18]=[C:17]([CH2:19][CH3:20])[O:16][N:15]=2)[O:7][C@H:6]1[N:21]1[CH:29]=[N:28][C:27]2[C:22]1=[N:23][C:24]([Cl:31])=[N:25][C:26]=2[NH:46][CH:43]([CH2:44][CH3:45])[CH2:41][CH3:42])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 120193-PentanamineHCID 81531DiisopropylethylamineHCID 18336820HCID 18336820, compound

Product 1

HCID 86588182HCID 86588182, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
50 °C

Procedure

(2R,3R,4 R,5R)-4-(acetyloxy)-2-(2,6-dichloro-9H-purin-9-yl)-5-(5-ethylisoxazol-3-yl)tetrahydrofuran-3-yl acetate (125 mg) was dissolved in isopropanol (5 ml) and the solution was treated with diisopropylethylamine (0.06 ml) followed by 1-ethylpropylamine (0.044 ml). The mixture was heated at 50° C. under nitrogen for 16 h. The solvent was removed in vacuo and the mixture partitioned between ethyl acetate and 1 M hydrochloric acid. The organic layers were washed with saturated sodium bicarbonate solution and brine, dried (MgSO4) and evaporated in vacuo. Purification by chromatography on silica gel (Varian Bondelut cartridge), eluting with (i) dichloromethane, (ii) ether and (iii) ethyl acetate, gave the title compound as a colourless oil (108 mg). TLC SiO2 (ether) Rf=0.26.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe mixture partitioned between ethyl acetate and 1 M hydrochloric acid
  3. washThe organic layers were washed with saturated sodium bicarbonate solution and brine
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo
  6. customPurification by chromatography on silica gel (Varian Bondelut cartridge)
  7. washeluting with (i) dichloromethane, (ii) ether and (iii) ethyl acetate

Sources & evidence

ORD record
ord-a054449c380840c2ba74d459ae1a0d5a
Source dataset
uspto-grants-2004_01
Patent number
US06677316B2

Reaction notes

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