HCID 86692728, compound → HCID 86692727, compound

HRID 1484611Notes

Reaction equation

HRID 1484611 reaction equation
[I:1][C:2]1[CH:35]=[CH:34][C:5]([CH2:6][N:7]([CH2:20][C:21]2[N:22]([CH2:26][C:27]([O:29]C(C)(C)C)=[O:28])[CH:23]=[CH:24][N:25]=2)[CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([S:16](=[O:19])(=[O:18])[NH2:17])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1>C(Cl)Cl.C(O)(C(F)(F)F)=O>[I:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]([CH2:20][C:21]2[N:22]([CH2:26][C:27]([OH:29])=[O:28])[CH:23]=[CH:24][N:25]=2)[CH2:8][CH2:9][C:10]2[CH:11]=[CH:12][C:13]([S:16](=[O:19])(=[O:18])[NH2:17])=[CH:14][CH:15]=2)=[CH:34][CH:35]=1

Participants

4

Reactant 1

HCID 86692728HCID 86692728, compound

Product 1

HCID 86692727HCID 86692727, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of tert-butyl 2-(2-(((4-iodobenzyl)(4-sulfamoylphenethyl)amino)methyl)-1H-imidazol-1-yl)acetate (24 mg, 0.0393 mmol) in DCM (1.0 mL) and TFA (1.0 mL) was stirred at room temperature for 5 hrs. Solvent was removed under a stream of nitrogen to give a residue, which was purified by HPLC to give compound (20) containing 2 TFA as a white solid (30 mg, 100%). 1H NMR (400 MHz, DMSO-d6) 7.68-7.57 (m, 6H), 7.26 (d, J=8.0 Hz, 2H), 7.25 (s, 2H), 7.13 (d, J=8.4 Hz, 2H), 4.90 (s, 2H), 3.94 (s, 2H), 3.67 (s, 2H), 2.80 (t, J=7.8 Hz, 2H), 2.55 (t, J=7.8 Hz, 2H); MS (ESI), 555.0 (M+H)−.

Workup

  1. customSolvent was removed under a stream of nitrogen
  2. customto give a residue, which
  3. customwas purified by HPLC

Sources & evidence

ORD record
ord-526140f768e24a1f974477446d692b71
Source dataset
uspto-grants-2016_08
Patent number
US09422251B2

Reaction notes

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