1,2-Dichloroethane → HCID 178481254, compound

HRID 230007Notes

Reaction equation

HRID 230007 reaction equation
[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([N:11]([CH2:23][C:24]2[CH:32]=[CH:31][C:27]([C:28]([OH:30])=O)=[CH:26][CH:25]=2)[C:12]2[N:16]([CH3:17])[C:15]3[CH:18]=[CH:19][C:20]([OH:22])=[CH:21][C:14]=3[N:13]=2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].O.[NH:34]1[C:38]([NH2:39])=[N:37][N:36]=[N:35]1.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.C(Cl)CCl>CN(C=O)C>[C:1]([CH:5]1[CH2:6][CH2:7][CH:8]([N:11]([CH2:23][C:24]2[CH:25]=[CH:26][C:27]([C:28]([NH:39][C:38]3[NH:37][N:36]=[N:35][N:34]=3)=[O:30])=[CH:31][CH:32]=2)[C:12]2[N:16]([CH3:17])[C:15]3[CH:18]=[CH:19][C:20]([OH:22])=[CH:21][C:14]=3[N:13]=2)[CH2:9][CH2:10]1)([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 688361734-{[(4-Tert-butylcyclohexyl)(5-hydroxy-1-methyl-1h-benzimidazol-2-yl)amino]methyl}benzoic acidHCID 178509300HCID 178509300, compound

Product 1

HCID 178481254HCID 178481254, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of the title compound of Example 15 Step B (0.02 mmol, 10 mg), 1H-tetraazol-5-amine monohydrate (0.2 mmol, 21 mg), HOBt (0.2 mmol, 31 mg) and DIEA (0.3 mmol, 52 μL) in 0.5 mL of DMF was added EDC (0.2 mmol, 38 mg). The reaction was heated to 40° C. 15 min, then allowed to stand at ambient temperature overnight. The reaction mixture was concentrated under reduced pressure. The residue was taken up in ca. 2:1 dioxane/H2O and acidified with TFA, then purified by reverse-phase chromatography (Condition B). The product was lyophilized affording the title compound as a white solid. MS (ESI): m/z 503 (M+H). HPLC A: 1.88 min.

Workup

  1. custom15 min
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. custompurified by reverse-phase chromatography (Condition B)

Sources & evidence

ORD record
ord-27b2d7bd8e024422a541cee6563365ea
Source dataset
uspto-grants-2009_07
Patent number
US07563815B2

Reaction notes

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