3-Fluorobenzylamine → HCID 16735278, compound

HRID 1474752Notes

Reaction equation

HRID 1474752 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@H:11]2[C@@H:15]([OH:16])[C@H:14]([OH:17])[CH2:13][S:12]2)=[C:4](Cl)[N:3]=1.[F:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH2:23][NH2:24]>C(O)C>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@H:11]2[C@H:15]([OH:16])[C@H:14]([OH:17])[CH2:13][S:12]2)=[C:4]([NH:24][CH2:23][C:22]2[CH:25]=[CH:26][CH:27]=[C:20]([F:19])[CH:21]=2)[N:3]=1

Participants

4

Reactant 2

HCID 668533-FluorobenzylamineHCID 86642172HCID 86642172, compound

Product 1

HCID 16735278HCID 16735278, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(2R,3S,4S)-2-(2,6-dichloro-9H-purin-9-yl)tetrahydrothiophen-3,4-diol (1 equivalent), prepared in Step 2, and 3-fluorobenzylamine (1.5 equivalents) were dissolved in ethanol (5 ml) at room temperature for 2-3 hrs with stirring. The reaction mixture was concentrated in a vacuum and the concentrate was purified through silica gel column chromatography using a mixture of dichloromethane:methanol (20:1, v/v) as an elution solvent to afford the object compound (0.10 g, 80%).

Workup

  1. concentrationThe reaction mixture was concentrated in a vacuum
  2. customthe concentrate was purified through silica gel column chromatography
  3. additiona mixture of dichloromethane:methanol (20:1

Sources & evidence

ORD record
ord-5bfcf2772d2d4dc7b94bf45ed1e75930
Source dataset
uspto-grants-2015_04
Patent number
US09018371B2

Reaction notes

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