di-tert-butyl 2,2'-((2-(2-((((1-(2-((3-iodophenyl)amino)-2-oxoethyl)-1H-imidazol-2-yl)methyl)(4-sulfamoylphenethyl)amino)methyl)-1H-imidazo 1-yl)acetyl)azanediyl)diacetate → 2,2'-((2-(2-((((1-(2-((3-iodophenyl)amino)-2-oxoethyl)-1H-imidazol-2-yl)methyl)(4-sulfamoylphenethyl)amino)methyl)-1H-imidazol-1-yl)acetyl)azanediyl)diacetic acid

HRID 1484609Notes

Reaction equation

HRID 1484609 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:56])[CH2:10][N:11]2[CH:15]=[CH:14][N:13]=[C:12]2[CH2:16][N:17]([CH2:30][C:31]2[N:32]([CH2:36][C:37]([N:39]([CH2:48][C:49]([O:51]C(C)(C)C)=[O:50])[CH2:40][C:41]([O:43]C(C)(C)C)=[O:42])=[O:38])[CH:33]=[CH:34][N:35]=2)[CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([S:26](=[O:29])(=[O:28])[NH2:27])=[CH:22][CH:21]=2)[CH:5]=[CH:6][CH:7]=1>C(Cl)Cl.C(O)(C(F)(F)F)=O>[I:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:56])[CH2:10][N:11]2[CH:15]=[CH:14][N:13]=[C:12]2[CH2:16][N:17]([CH2:30][C:31]2[N:32]([CH2:36][C:37]([N:39]([CH2:48][C:49]([OH:51])=[O:50])[CH2:40][C:41]([OH:43])=[O:42])=[O:38])[CH:33]=[CH:34][N:35]=2)[CH2:18][CH2:19][C:20]2[CH:21]=[CH:22][C:23]([S:26](=[O:28])(=[O:29])[NH2:27])=[CH:24][CH:25]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 86692723di-tert-butyl 2,2'-((2-(2-((((1-(2-((3-iodophenyl)amino)-2-oxoethyl)-1H-imidazol-2-yl)methyl)(4-sulfamoylphenethyl)amino)methyl)-1H-imidazo 1-yl)acetyl)azanediyl)diacetate

Product 1

HCID 866927242,2'-((2-(2-((((1-(2-((3-iodophenyl)amino)-2-oxoethyl)-1H-imidazol-2-yl)methyl)(4-sulfamoylphenethyl)amino)methyl)-1H-imidazol-1-yl)acetyl)azanediyl)diacetic acidYield 74%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of di-tert-butyl 2,2′-((2-(2-((((1-(2-((3-iodophenyl)amino)-2-oxoethyl)-1H-imidazol-2-yl)methyl)(4-sulfamoylphenethyl)amino)methyl)-1H-imidazol-1-yl)acetyl)azanediyl)diacetate (45 mg, 0.0497 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 (18) as a white solid (29 mg, 74%). 1H NMR (400 MHz, DMSO-d6) 10.69 (s, 0.66H), 10.61 (s, 0.34H), 8.10 (s, 0.66H), 8.07 (s, 0.34H), 7.69-7.62 (m, 3H), 7.54 (s, 1H), 7.48-7.44 (m, 2H), 7.27 (s, 2H), 7.30-7.26 (m, 3H), 7.13 (t, J=8.0 Hz, 1H), 5.31 (s, 1.32H), 5.15 (s, 1.32H), 5.12 (s, 0.68H), 4.75 (s, 0.68H), 4.33 (s, 2H), 4.16 (s, 2H), 4.05 (s, 4H), 2.72-2.68 (m, 4H); MS (ESI), 793.1 (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-5dd0a2b48d964187b0a3bef4e0e3152a
Source dataset
uspto-grants-2016_08
Patent number
US09422251B2

Reaction notes

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