3-Fluorobenzylamine → HCID 25002987, compound

HRID 1474753Notes

Reaction equation

HRID 1474753 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:15]([OH:16])[C@H:14]([OH:17])[CH2:13][S:12]1.[F:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH2:22][NH2:23]>C(O)C>[F:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH2:22][NH:23][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:15]([OH:16])[C@H:14]([OH:17])[CH2:13][S:12]1

Participants

4

Reactant 2

HCID 668533-FluorobenzylamineHCID 86642173HCID 86642173, compound

Product 1

HCID 25002987HCID 25002987, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(2R,3S,4S)-2-(6-chloro-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 (0.11 g, 82%).

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-9187daa680bb4890bb1e551e4c0af251
Source dataset
uspto-grants-2015_04
Patent number
US09018371B2

Reaction notes

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