4-[5-(4-Chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-benzene-1,2-diamine → 3-(3,5-Dichloro-4-{6-[5-(4-chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-1H-benzoimidazol-2-yl}-phenyl)-propionic acid tert-butyl ester

HRID 1513293Notes

Reaction equation

HRID 1513293 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11]([C:13]3[CH:14]=[C:15]([NH2:20])[C:16]([NH2:19])=[CH:17][CH:18]=3)=[N:10][N:9]=2)=[CH:4][CH:3]=1.[C:21]([O:25][C:26](=[O:39])[CH2:27][CH2:28][C:29]1[CH:34]=[C:33]([Cl:35])[C:32]([CH:36]=O)=[C:31]([Cl:38])[CH:30]=1)([CH3:24])([CH3:23])[CH3:22]>CS(C)=O>[C:21]([O:25][C:26](=[O:39])[CH2:27][CH2:28][C:29]1[CH:34]=[C:33]([Cl:35])[C:32]([C:36]2[NH:20][C:15]3[CH:14]=[C:13]([C:11]4[O:12][C:8]([C:5]5[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=5)=[N:9][N:10]=4)[CH:18]=[CH:17][C:16]=3[N:19]=2)=[C:31]([Cl:38])[CH:30]=1)([CH3:24])([CH3:22])[CH3:23]

Participants

4

Reactant 2

HCID 669664354-[5-(4-Chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-benzene-1,2-diamineHCID 866328253-(3,5-Dichloro-4-formylphenyl)-propionic acid tert-butyl ester

Product 1

HCID 669665013-(3,5-Dichloro-4-{6-[5-(4-chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-1H-benzoimidazol-2-yl}-phenyl)-propionic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a 20 ml scint. vial was added 0.3783 g (1.32 mmol) 4- [5-(4-Chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-benzene-1,2-diamine, 04000 g (01.32 mmol) of 3-(3,5-Dichloro-4-formyl-phenyl)-propionic acid tert-butyl ester (step A), and 6 mL of DMSO. To this dark brown solution was added 0.0321 g (0.198 mmol) of FeCl3. Allowed to stir open to air for 72 h. Extracted with EtOAc, and washed with water, brine and dried with Na2SO4. Purified on silica gel (ACN/DCM, 1:9 to 4:6) to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.39 (s, 9 H) 2.64 (t, J=7.33 Hz, 2 H) 2.92 (t, J=7.26 Hz, 2H) 7.60 (s, 2 H) 7.72 (d, 2 H) 7.78 (d, J=8.59 Hz, 0.5 H) 7.92 (d, J=8.46 Hz, 0.5 H) 8.00-8.09 (m, 1 H) 8.17-8.22 (m, 2 H) 8.31 (s, 0.5 H) 8.50 (s, 0.5 H) 13.32 (d, J=11.24 Hz, 1 H). MS (m/z) 571.1 M (+1), tR=1.59, Meth 10

Workup

  1. extractionExtracted with EtOAc
  2. washwashed with water, brine
  3. dry with materialdried with Na2SO4
  4. customPurified on silica gel (ACN/DCM, 1:9 to 4:6)

Sources & evidence

ORD record
ord-7697ad73f67f4ee0a6b4836579cd4239
Source dataset
uspto-grants-2012_07
Patent number
US08217065B2

Reaction notes

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