HCID 86692726, compound → HCID 86692725, compound

HRID 2273351Notes

Reaction equation

HRID 2273351 reaction equation
[I:1][C:2]1[CH:47]=[CH:46][C:5]([CH2:6][N:7]([CH2:20][C:21]2[N:22]([CH2:26][C:27]([N:29]([CH2:38][C:39]([O:41]C(C)(C)C)=[O:40])[CH2:30][C:31]([O:33]C(C)(C)C)=[O:32])=[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:47]=[CH:46][C:5]([CH2:6][N:7]([CH2:20][C:21]2[N:22]([CH2:26][C:27]([N:29]([CH2:30][C:31]([OH:33])=[O:32])[CH2:38][C:39]([OH:41])=[O:40])=[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:4][CH:3]=1

Participants

4

Reactant 1

HCID 86692726HCID 86692726, compound

Product 1

HCID 86692725HCID 86692725, compoundYield 104.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of di-tert-butyl 2,2′-((2-(2-(((4-iodobenzyl)(4-sulfamoylphenethyl)amino)methyl)-1H-imidazol-1-yl)acetyl)azanediyl)diacetate (28.8 mg, 0.0369 mmol) in DCM (0.50 mL) and TFA (0.5 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 (19) as a white solid (25.9 mg, 78.2%). 1H NMR (400 MHz, DMSO-d6) 7.70-7.66 (m, 4H), 7.57 (s, 1H), 7.55 (s, 1H), 7.29 (d, J=8.0 Hz, 2H), 7.28 (s, 2H), 7.17 (d, J=8.0 Hz, 2H), 5.26 (s, 2H), 4.34 (s, 2H), 4.06 (s, 2H), 3.91 (s, 2H), 3.69 (s, 2H), 2.82 (t, J=7.8 Hz, 2H), 2.59 (t, J=7.6 Hz, 2H); MS (ESI), 670.1 (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-50760f4d71aa40518f44c51a2acfb9b1
Source dataset
uspto-grants-2015_09
Patent number
US09120837B2

Reaction notes

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