3-Pentanamine → {(1S,4R)-4-[2-Chloro-6-(1-ethyl-propylamino)-purin-9-yl]-cyclopent-2-enyl}-propionyl-carbamic acid tert-butyl ester

HRID 1696993Notes

Reaction equation

HRID 1696993 reaction equation
[C:1]([O:5][C:6](=[O:28])[N:7]([C@H:12]1[CH2:16][C@@H:15]([N:17]2[CH:25]=[N:24][C:23]3[C:18]2=[N:19][C:20]([Cl:27])=[N:21][C:22]=3Cl)[CH:14]=[CH:13]1)[C:8](=[O:11])[CH2:9][CH3:10])([CH3:4])([CH3:3])[CH3:2].[CH3:29][CH2:30][CH:31]([NH2:34])[CH2:32][CH3:33]>C1COCC1>[C:1]([O:5][C:6](=[O:28])[N:7]([C@H:12]1[CH2:16][C@@H:15]([N:17]2[CH:25]=[N:24][C:23]3[C:18]2=[N:19][C:20]([Cl:27])=[N:21][C:22]=3[NH:34][CH:31]([CH2:32][CH3:33])[CH2:30][CH3:29])[CH:14]=[CH:13]1)[C:8](=[O:11])[CH2:9][CH3:10])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 120193-PentanamineHCID 86622633[(1S,4R)-4-(2,6-Dichloro-purin-9-yl)-cyclopent-2-enyl]-propionyl-carbamic acid tert-butyl ester

Product 1

HCID 86622634{(1S,4R)-4-[2-Chloro-6-(1-ethyl-propylamino)-purin-9-yl]-cyclopent-2-enyl}-propionyl-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

[(1S,4R)-4-(2,6-Dichloro-purin-9-yl)-cyclopent-2-enyl]-propionyl-carbamic acid tert-butyl ester (700 mg, 1.64 mmol) is dissolved in THF (15 ml) under an atmosphere of argon. 3-Pentyl-amine (315 mg, 3.61 mmol) is added and the reaction mixture is stirred at 50° C. The reaction is shown to be complete by LCMS after 18 hours. The reaction mixture is partitioned between dichloromethane (50 ml) and 0.1M HCl (50 ml). The organic layer is washed with water (20 ml) and brine (20 ml), dried over MgSO4, filtered and the solvent is removed in vacuo to give the title compound. 1H nmr (CDCl3, 400 MHz); 8.10(s, 1H), 6.00(m, 1H), 5.70(m, 1H), 5.60(m, 2H), 5.45(m, 1H), 4.20(m, 1H), 3.65(m, 1H), 3.00(m, 1H), 2.65(m, 3H), 1.95(m, 1H), 1.60(m, 3H), 1.45(s, 9H), 1.10(m, 4H), 0.85(t, 6H), MS (ES+) m/e 477 (MH+).

Workup

  1. customThe reaction mixture is partitioned between dichloromethane (50 ml) and 0.1M HCl (50 ml)
  2. washThe organic layer is washed with water (20 ml) and brine (20 ml)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-64aa5e6737bc45eb812a5aec1a815df7
Source dataset
uspto-grants-2012_04
Patent number
US08163754B2

Reaction notes

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