1,2-Dichloroethane → HCID 178441008, compound

HRID 229995Notes

Reaction equation

HRID 229995 reaction equation
[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([N:11]([CH2:24][C:25]2[CH:33]=[CH:32][C:28]([C:29]([OH:31])=O)=[CH:27][CH:26]=2)[C:12]2[N:16]([CH2:17][CH2:18][OH:19])[C:15]3[CH:20]=[CH:21][CH:22]=[CH:23][C:14]=3[N:13]=2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].O.[NH:35]1[C:39]([NH2:40])=[N:38][N:37]=[N:36]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]([CH2:24][C:25]2[CH:26]=[CH:27][C:28]([C:29]([NH:40][C:39]3[NH:38][N:37]=[N:36][N:35]=3)=[O:31])=[CH:32][CH:33]=2)[C:12]2[N:16]([CH2:17][CH2:18][OH:19])[C:15]3[CH:20]=[CH:21][CH:22]=[CH:23][C:14]=3[N:13]=2)[CH2:9][CH2:10]1)([CH3:3])([CH3:4])[CH3:2]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 68837898HCID 68837898, compoundHCID 178509300HCID 178509300, compound

Product 1

HCID 178441008HCID 178441008, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the title compound of Example 10 Step B (0.04 mmol, 19 mg) 1H-tetraazol-5-amine monohydrate (0.13 mmol, 13 mg), HOBt (0.085 mmol, 13 mg) and EDC (0.17 mmol, 33 mg) in 0.5 mL of DMF was added DIEA (0.21 mmol, 36 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 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 517 (M+H). HPLC A: 1.81 min.

Workup

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

Sources & evidence

ORD record
ord-131c5d630577494eb04e6d088c9a28db
Source dataset
uspto-grants-2009_07
Patent number
US07563815B2

Reaction notes

Loading…