1,2-Dichloroethane → HCID 178481255, compound

HRID 230012Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([N:9]([CH2:20][C:21]2[CH:29]=[CH:28][C:24]([C:25]([OH:27])=O)=[CH:23][CH:22]=2)[C:10]2[N:14]([CH3:15])[C:13]3[CH:16]=[CH:17][CH:18]=[CH:19][C:12]=3[N:11]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.O.[NH:31]1[C:35]([NH2:36])=[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>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]([CH2:20][C:21]2[CH:29]=[CH:28][C:24]([C:25]([NH:36][C:35]3[NH:34][N:33]=[N:32][N:31]=3)=[O:27])=[CH:23][CH:22]=2)[C:10]2[N:14]([CH3:15])[C:13]3[CH:16]=[CH:17][CH:18]=[CH:19][C:12]=3[N:11]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of the title compound of Example 223 Step C (0.16 mmol, 68 mg), 1H-tetraazol-5-amine monohydrate (0.48 mmol, 49 mg), HOBt (0.32 mmol, 49 mg) and EDC (0.32 mmol, 61 mg) in 1 mL of DMF was added DIEA (0.48 mmol, 83 μL). The reaction mixture was warmed to 40° C. for 2 h, then concentrated under reduced pressure. The residue was purified by reverse-phase chromatography (Condition B). The product was lyophilized, affording a white solid. 1H NMR (500 MHz, d6-DMSO) δ 12.38 (s, 1H), 8.07 (d, 2H), 7.73 (d, 2H), 7.63 (m, 1H), 7.56 (m, 1H), 7.24-7.33 (overlapping m, 2H), 7.15 (t, 1H), 6.90 (d, 2H), 5.31 (s, 2H), 3.53 (s, 3H). MS (ESI): m/z 493 (M+H). HPLC A: 1.69 min.

Workup

concentrationconcentrated under reduced pressure
customThe residue was purified by reverse-phase chromatography (Condition B)
customaffording a white solid
custom1.69 min.

Sources & evidence

ORD record: ord-8fe433d32bfa4782b6dda9c8b954088c
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07563815B2

Reaction notes

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