1,2-Dichloroethane → HCID 178481256, compound

HRID 229992Notes

Reaction equation

HRID 229992 reaction equation
[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([N:11]([CH2:22][C:23]2[CH:31]=[CH:30][C:26]([C:27](O)=[O:28])=[CH:25][CH:24]=2)[C:12]2[N:16]([CH3:17])[C:15]3[CH:18]=[CH:19][CH:20]=[CH:21][C:14]=3[N:13]=2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[NH:32]1[C:36]([CH2:37][NH2:38])=[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>[C:1]([CH:5]1[CH2:6][CH2:7][CH:8]([N:11]([CH2:22][C:23]2[CH:24]=[CH:25][C:26]([C:27]([NH:38][CH2:37][C:36]3[NH:35][N:34]=[N:33][N:32]=3)=[O:28])=[CH:30][CH:31]=2)[C:12]2[N:16]([CH3:17])[C:15]3[CH:18]=[CH:19][CH:20]=[CH:21][C:14]=3[N:13]=2)[CH2:9][CH2:10]1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 688367154-{[(4-tert-Butylcyclohexyl)(1-methyl-1H-benzimidazol-2-yl)amino]methyl}-benzoic acidHCID 178510704HCID 178510704, compound

Product 1

HCID 178481256HCID 178481256, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the title compound of Example 5 Step A (0.06 mmol, 25 mg) 1H-tetraazol-5-ylmethylamine (0.09 mmol, 12 mg), HOBt (0.15 mmol, 23 mg) and EDC (0.18 mmol, 35 mg) in 0.5 mL of DMF was added DIEA (0.3 mmol, 52 μL). The reaction was allowed to proceed overnight at ambient temperature. The mixture was partitioned between EtOAc/brine. The organic phase was concentrated under reduced pressure and the residue was purified by reverse-phase chromatography (Condition A) and lyophilized, affording the title compound as a white solid. MS (ESI): m/z 517 (M+H). HPLC A: 1.94 min.

Workup

  1. customThe mixture was partitioned between EtOAc/brine
  2. concentrationThe organic phase was concentrated under reduced pressure
  3. customthe residue was purified by reverse-phase chromatography (Condition A) and

Sources & evidence

ORD record
ord-beb39591e72448409fed3e1bb7851222
Source dataset
uspto-grants-2009_07
Patent number
US07563815B2

Reaction notes

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