1,8-Diazabicyclo(5.4.0)undec-7-ene → (S)-N-(5-(3-(hydroxymethyl)-5-(trifluoromethyl)benzyl)-2,3-dihydro-1H-inden-2-yl)methanesulfonamide

HRID 473109Notes

Reaction equation

HRID 473109 reaction equation
[NH2:1][C@@H:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:11][C:12]3[CH:13]=[C:14]([CH2:22][OH:23])[CH:15]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:17]=3)[CH:8]=2)[CH2:3]1.[CH3:24][S:25](OC1C(F)=C(F)C(F)=C(F)C=1F)(=[O:27])=[O:26].N1CCCN2CCCCCC=12>C1COCC1>[OH:23][CH2:22][C:14]1[CH:13]=[C:12]([CH:17]=[C:16]([C:18]([F:19])([F:20])[F:21])[CH:15]=1)[CH2:11][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[CH2:3][C@H:2]([NH:1][S:25]([CH3:24])(=[O:27])=[O:26])[CH2:10]2

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2783233Perfluorophenyl methanesulfonateHCID 66733722(S)-(3-((2-amino-2,3-dihydro-1H-inden-5-yl)methyl)-5-(trifluoromethyl)phenyl)methanol

Product 1

HCID 70222665(S)-N-(5-(3-(hydroxymethyl)-5-(trifluoromethyl)benzyl)-2,3-dihydro-1H-inden-2-yl)methanesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To (S)-(3-((2-amino-2,3-dihydro-1H-inden-5-yl)methyl)-5-(trifluoromethyl)phenyl)methanol (50, mg, 0.16 mmol) in THF (1 mL) was added perfluorophenyl methanesulfonate (39 mg, 0.15 mmol) followed by 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine (34.1 mg 0.22 mmol). The reaction was allowed to stir at RT overnight before removing the solvent in vacuo. The sample was redissolved in DMSO (500 μL) before purifying by reverse phase preparative HPLC-MS to give the title compound as a clear film (11 mg, 17.2%). MS (ESI): m/z [M+H]+ 400.1

Workup

  1. custombefore removing the solvent in vacuo
  2. dissolutionThe sample was redissolved in DMSO (500 μL)
  3. custombefore purifying by reverse phase preparative HPLC-MS

Sources & evidence

ORD record
ord-96116dae59a445a8b8af620b65340a69
Source dataset
uspto-grants-2014_01
Patent number
US08633237B2

Reaction notes

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