1,2-Dichloroethane → HCID 178441009, compound

HRID 229984Notes

Reaction equation

HRID 229984 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]([CH2:21][C:22]1[CH:30]=[CH:29][C:25]([C:26]([OH:28])=O)=[CH:24][CH:23]=1)[CH:11]1[CH2:16][CH2:15][CH:14]([C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:13][CH2:12]1.O.[NH:32]1[C:36]([NH2:37])=[N:35][N:34]=[N:33]1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.CCN(C(C)C)C(C)C>CN(C=O)C>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]([CH2:21][C:22]1[CH:30]=[CH:29][C:25]([C:26]([NH:37][C:36]2[NH:35][N:34]=[N:33][N:32]=2)=[O:28])=[CH:24][CH:23]=1)[CH:11]1[CH2:12][CH2:13][CH:14]([C:17]([CH3:18])([CH3:20])[CH3:19])[CH2:15][CH2:16]1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 688356554-{[1h-Benzimidazol-2-yl(4-tert-butylcyclohexyl)amino]methyl}benzoic acidHCID 178509300HCID 178509300, compound

Product 1

HCID 178441009HCID 178441009, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the title compound of Example 1 Step D (0.1 mmol, 41 mg), 1H-tetraazol-5-amine monohydrate (0.2 mmol, 21 mg), HOBt (0.25 mmol, 38 mg) and EDC (0.4 mmol, 77 mg) in 1 mL of DMF was added DIEA (0.5 mmol, 90 μL). The reaction mixture was allowed to stand at ambient temperature overnight, then concentrated under reduced pressure. The residue was taken up in ca. 2:1 dioxane/H2O, acidified with TFA, and purified by reverse-phase chromatography (Condition A). Lyophilization afforded the product as a white solid. MS (ESI): m/z 473 (M+H). HPLC A: 1.86 min.

Workup

  1. concentrationconcentrated under reduced pressure
  2. custompurified by reverse-phase chromatography (Condition A)

Sources & evidence

ORD record
ord-b01727d900174c28bb3b64a0cb95989e
Source dataset
uspto-grants-2009_07
Patent number
US07563815B2

Reaction notes

Loading…