Acetic Acid → HCID 178514786, compound

HRID 415854Notes

Reaction equation

I.[NH2:2][CH2:3][CH2:4][NH:5][C:6]1[C:7]([C:11]2[N:15]([CH2:16][C:17]3[O:18][CH:19]=[C:20]([Br:22])[CH:21]=3)C(=O)[O:13][N:12]=2)=[N:8][O:9][N:10]=1.[S:24](N)([NH2:27])(=[O:26])=[O:25].[OH-].[Na+].O.C(O)(=O)C>N1C=CC=CC=1>[NH2:27][S:24]([NH:2][CH2:3][CH2:4][NH:5][C:6]1[C:7]([C:11](=[N:12][OH:13])[NH:15][CH2:16][C:17]2[O:18][CH:19]=[C:20]([Br:22])[CH:21]=2)=[N:8][O:9][N:10]=1)(=[O:26])=[O:25]

Participants

Conditions

Temperature: 130 °C

Procedure

In a microwave vial, 3-{4-[(2-aminoethyl)amino]-1,2,5-oxadiazol-3-yl}-4-[(4-bromo-2-furyl)methyl]-1,2,4-oxadiazol-5(4H)-one hydroiodide (30 mg, 0.060 mmol) and sulfamide (29 mg, 0.30 mmol) were suspended in pyridine (1 mL). The reaction mixture was flushed with nitrogen and heated at 130° C. for 3 minutes in a microwave reactor. The solvent was removed and the crude intermediate was suspended in methanol (1 mL). A 2.0 N solution of NaOH in water (0.30 mL, 0.60 mmol) was added in one portion and the reaction was heated to 45° C. for 30 minutes. After neutralization with acetic acid (68 μL, 1.2 mmol), the product was purified by preparative LCMS to give the desired product (10.4 mg, 41%). LCMS calculated for C10H15BrN7O5S (M+H): m/z=423.9, 426.0. 1H NMR (400 MHz, DMSO-d6): δ 10.87 (s, 1H), 7.75 (s, 1H), 6.83 (t, J=7.3 Hz, 1H), 6.68 (t, J=6.0 Hz, 1H), 6.56 (s, 2H), 6.30 (t, J=6.0 Hz, 1H), 6.23 (s, 1H), 4.56 (d, J=7.0 Hz, 2H), 3.32 (q, J=6.3 Hz, 2H), 3.07 (q, J=6.3 Hz, 2H).

Workup

customThe reaction mixture was flushed with nitrogen
customThe solvent was removed
temperaturethe reaction was heated to 45° C. for 30 minutes

Sources & evidence

ORD record: ord-cf568aef19ca4efd9fb805ed1c5fc601
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088803B2

Reaction notes

Loading…