Cyclopentylamine → HCID 67190843, compound

HRID 496549Notes

Reaction equation

HRID 496549 reaction equation
Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@H:11]1[C@H:18]2[C@@H:14]([O:15][C:16]([CH3:20])([CH3:19])[O:17]2)[C@@H:13]([CH2:21][S:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[F:29])[O:12]1.[CH:30]1([NH2:35])[CH2:34][CH2:33][CH2:32][CH2:31]1>C(O)C.C(N(CC)CC)C>[F:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[S:22][CH2:21][C@@H:13]1[C@H:14]2[C@@H:18]([O:17][C:16]([CH3:20])([CH3:19])[O:15]2)[C@H:11]([N:6]2[CH:5]=[N:4][C:3]3[C:7]2=[N:8][CH:9]=[N:10][C:2]=3[NH:35][CH:30]2[CH2:34][CH2:33][CH2:32][CH2:31]2)[O:12]1

Participants

5

Reactant 2

HCID 2906CyclopentylamineHCID 86587415HCID 86587415, compound

Product 1

HCID 67190843HCID 67190843, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 1-{[(2S,1R,4R,5R)-4-(6-chloropurin-9-yl)-7,7-dimethyl-3,6,8-trioxabicyclo[3.3.0]oct-2-yl]methylthio}-2-fluorobenzene, a compound of formula (3), (0.125 g, 2.86 mmoles) in 10 mL of ethanol and 1 mL of triethylamine was added cyclopentylamine in excess, and the mixture refluxed under nitrogen for 24 hours. The solvent was removed under reduced pressure, and the residue was purified by preparative TLC using 1:1 EtOAc:Hexanes to give (9-{(4S,1R,2R,5R)-4-[(2-fluorophenylthio)methyl]-7,7-dimethyl-3,6,8-trioxabicyclo[3.3.0]oct-2-yl}purin-6-yl)cyclopentylamine, a compound of formula (4), as a yellow oil (80 mg, 56%) 1H NMR (CDCl3) δ 1.4 (s, 3H), 1.6 (s, 3H), 1.6-2.4 (m, 6H), 3.15-3.25 (m, 2H), 4.1 (bs, 1H), 4.4 (t, 1H), 5.1 (m, 1H), 5.5 (m, 1H), 6.0 (d, 1H), 6.2 (bs, 1H), 7.0 (m, 2H), 7.2 (m, 1H), 7.4 (m, 1H), 7.8 (s, 1H), 8.25 (s, 1H).

Workup

  1. temperaturerefluxed under nitrogen for 24 hours
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-16b18775c79d4e0396e22d9ec660741e
Source dataset
uspto-grants-2005_09
Patent number
US06946449B2

Reaction notes

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