1,2-Dichloroethane → HCID 178441010, compound

HRID 229986Notes

Reaction equation

HRID 229986 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.[NH:31]1[C:35]([CH2:36][NH2:37])=[N:34][N:33]=[N:32]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][CH2:36][C:35]2[NH:34][N:33]=[N:32][N:31]=2)=[O:28])=[CH:24][CH:23]=1)[CH:11]1[CH2:12][CH2:13][CH:14]([C:17]([CH3:20])([CH3:19])[CH3:18])[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 178510704HCID 178510704, compound

Product 1

HCID 178441010HCID 178441010, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the title compound of Example 1 Step D (0.04 mmol, 16 mg), 1H-tetraazol-5-ylmethylamine (0.06 mmol, 8 mg), HOBt (0.1 mmol, 15 mg) and EDC (0.12 mmol, 23 mg) in 0.4 mL of DMF was added DIEA (0.2 mmol, 35 μL). After 3 h the reaction mixture was concentrated under reduced pressure. The product was purified by reverse-phase chromatography (Condition A) and lyophilized, affording the title compound as a white solid. MS (ESI): m/z 487 (M+H). HPLC A: 1.58 min.

Workup

  1. concentrationAfter 3 h the reaction mixture was concentrated under reduced pressure
  2. customThe product was purified by reverse-phase chromatography (Condition A) and

Sources & evidence

ORD record
ord-9ebd1b11312544dca2efcd23f8bd0694
Source dataset
uspto-grants-2009_07
Patent number
US07563815B2

Reaction notes

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