Water → HCID 178510222, compound

HRID 2402241Notes

Reaction equation

I.[NH2:2][CH2:3][CH2:4][NH:5][C:6]1[C:7]([C:11]2[N:15]([C:16]3[CH:17]=[CH:18][C:19]([F:24])=[C:20]([CH:23]=3)[C:21]#[N:22])C(=O)[O:13][N:12]=2)=[N:8][O:9][N:10]=1.[S:26](N)([NH2:29])(=[O:28])=[O:27].[OH-].[Na+].O>N1C=CC=CC=1>[NH2:29][S:26]([NH:2][CH2:3][CH2:4][NH:5][C:6]1[C:7]([C:11](=[N:12][OH:13])[NH:15][C:16]2[CH:17]=[CH:18][C:19]([F:24])=[C:20]([C:21]#[N:22])[CH:23]=2)=[N:8][O:9][N:10]=1)(=[O:28])=[O:27]

Participants

Conditions

Temperature: 120 °C

Procedure

In a microwave vial, 5-[3-{4-[(2-aminoethyl)amino]-1,2,5-oxadiazol-3-yl}-5-oxo-1,2,4-oxadiazol-4(5H)-yl]-2-fluorobenzonitrile hydroiodide (20.0 mg, 0.044 mmol) and sulfamide (25 mg, 0.26 mmol) were suspended in pyridine (0.5 mL). The reaction was heated to 120° C. for 10 minutes in a microwave reactor. The solvent was removed and the residue dissolved in methanol (0.17 mL). A solution of 2.0 N NaOH in water (0.22 mL, 0.44 mmol) was added in one portion. The reaction was stirred at room temperature overnight. After neutralization with acetic acid (50 μL), the product was purified using preparative LCMS to give the title compound (4.9 mg, 29%). LCMS for C12H14FN8O4S (M+H)+: m/z=385.0. 1H NMR (400 MHz, DMSO-d6): δ 11.65 (s, 1H), 9.08 (s, 1H), 7.34 (t, J=9.1 Hz, 1H), 7.22 (dd, J=5.4, 2.8 Hz, 1H), 7.13 (m, 1H), 6.70 (t, J=5.9 Hz, 1H), 6.59 (s, 2H), 6.20 (t, J=6.1 Hz, 1H), 3.34 (m, 2H), 3.09 (m, 2H).

Workup

customThe solvent was removed
dissolutionthe residue dissolved in methanol (0.17 mL)
customAfter neutralization with acetic acid (50 μL), the product was purified

Sources & evidence

ORD record: ord-16c8cfa3f5f74aa885f9da5f8e284082
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08796319B2

Reaction notes

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