Triethylamine → HCID 11648790, compound

HRID 914726Notes

Reaction equation

HRID 914726 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([N:9]2[CH2:13][CH2:12][C@H:11]([NH2:14])[CH2:10]2)[CH:6]=[CH:7][CH:8]=1.Cl[C:16]1[N:24]=[CH:23][N:22]=[C:21]2[C:17]=1[N:18]=[CH:19][N:20]2[C@H:25]1[C@H:32]2[C@H:28]([O:29][C:30]([CH3:34])([CH3:33])[O:31]2)[C@@H:27]([CH2:35][F:36])[CH2:26]1.CCN(CC)CC>CCO>[Cl:2][C:3]1[CH:4]=[C:5]([N:9]2[CH2:13][CH2:12][C@H:11]([NH:14][C:16]3[N:24]=[CH:23][N:22]=[C:21]4[C:17]=3[N:18]=[CH:19][N:20]4[C@H:25]3[C@H:32]4[C@H:28]([O:29][C:30]([CH3:33])([CH3:34])[O:31]4)[C@@H:27]([CH2:35][F:36])[CH2:26]3)[CH2:10]2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9973677HCID 9973677, compoundHCID 69421553HCID 69421553, compound

Product 1

HCID 11648790HCID 11648790, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(3-Chloro-phenyl)-pyrrolidin-3(S)-ylamine hydrochloride (300 mg, 1.29 mmoles) prepared as in step 4 of example 1 and 6-chloro-9-((3aS,4R,6S,6aR)-6-fluoromethyl-2,2-dimethyl-tetrahydro-cyclopenta-1,3-dioxol-4-yl)-9H-purine (420 mg, 1.29 mmoles) prepared as described above were combined in EtOH (12 ml), NEt3 (730 μl, 5.15 mmoles) was then added and the resulting brown solution was stirred at reflux under an argon atmosphere. After 22 h, the reaction mixture was cooled to room temperature, evaporated to dryness, the residue was partitioned between water and EtOAc, the aqueous layer was separated and extracted two times with EtOAc. The combined organic layers are washed with brine and dried over magnesium sulfate. The filtrate is concentrated under reduced pressure to give a residue which is purified by flash chromatography on silica gel eluting with 40% EtOAc in cyclohexane followed by 5% MeOH in CH2Cl2 to yield [(S)-1-(3-chloro-phenyl)-pyrrolidin-3-yl]-[9-((3aS,4R,6S,6aR)-6-fluoromethyl-2,2-dimethyl -tetrahydro-cyclopenta-1,3-dioxol-4-yl)-9H-purin-6-yl]-amine

Workup

  1. customprepared
  2. temperatureat reflux under an argon atmosphere
  3. customevaporated to dryness
  4. customthe residue was partitioned between water and EtOAc
  5. customthe aqueous layer was separated
  6. extractionextracted two times with EtOAc
  7. washThe combined organic layers are washed with brine
  8. dry with materialdried over magnesium sulfate
  9. concentrationThe filtrate is concentrated under reduced pressure
  10. customto give a residue which
  11. customis purified by flash chromatography on silica gel eluting with 40% EtOAc in cyclohexane

Sources & evidence

ORD record
ord-59206f1dddeb4efc98fd8b987015d5bb
Source dataset
uspto-grants-2007_09
Patent number
US07265111B2

Reaction notes

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