1,2-Dichloroethane → HCID 178481253, compound

HRID 229999Notes

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]=[C:19]([OH:22])[CH:20]=[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.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]([CH2:23][C:24]2[CH:32]=[CH:31][C:27]([C:28]([NH:39][C:38]3[NH:37][N:36]=[N:35][N:34]=3)=[O:30])=[CH:26][CH:25]=2)[C:12]2[N:16]([CH3:17])[C:15]3[CH:18]=[C:19]([OH:22])[CH:20]=[CH:21][C:14]=3[N:13]=2)[CH2:9][CH2:10]1)([CH3:2])([CH3:4])[CH3:3]

Participants

Conditions

Temperature: 40 °C

Procedure

To the product of Example 12 Step B (0.04 mmol), 1H-tetraazol-5-amine monohydrate (0.12 mmol, 12 mg), HOBt (0.08 mmol, 12 mg) and EDC (0.08 mmol, 15 mg) in 1 mL of DMF was added DIEA (0.08 mmol, 14 μL). The reaction was heated at 40° C. for 2.5 h, 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 directly, affording the title compound as a white solid. 1H NMR (500 MHz, d6-DMSO): δ 12.35 (br s, 1H), 9.81 (br s, 1H), 8.01 (d, 2H), 7.52 (d, 2H), 7.28 (d, 2H), 6.91 (unres. d, 1H), 6.79 (dd, 1H), 4.75 (s, 2H), 3.69 (s, 3H), 2.01 (m, 2H), 1.83 (m, 2H), 1.69 (m, 2H), 1.16 (m, 2H), 1.04 (m, 11H), 0.85 (s, 9H). One proton obscured by H2O. MS (ESI): m/z 503 (M+H). HPLC A: 1.85 min.

Workup

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

Sources & evidence

ORD record: ord-ce930d3ca63042049449ce2a7584bf76
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07563815B2

Reaction notes

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