Cyclopentylamine → HCID 67190843, compound

HRID 2234745Notes

Reaction equation

HRID 2234745 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%)

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-2187591f83c74e79b39b003d48e1ce09
Source dataset
uspto-grants-2010_05
Patent number
US07713946B2

Reaction notes

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