Sodium Hydroxide → HCID 178514780, compound

HRID 2097663Notes

Reaction equation

FC(F)(F)C(O)=O.[NH2:8][CH2:9][CH2:10][CH2:11][C:12]1[C:13]([C:17]2[N:21]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[C:24]([Cl:29])[CH:23]=3)C(=O)[O:19][N:18]=2)=[N:14][O:15][N:16]=1.[S:31](N)([NH2:34])(=[O:33])=[O:32].[OH-].[Na+]>N1C=CC=CC=1.O>[NH2:34][S:31]([NH:8][CH2:9][CH2:10][CH2:11][C:12]1[C:13]([C:17](=[N:18][OH:19])[NH:21][C:22]2[CH:27]=[CH:26][C:25]([F:28])=[C:24]([Cl:29])[CH:23]=2)=[N:14][O:15][N:16]=1)(=[O:33])=[O:32]

Participants

Conditions

Temperature: 120 °C

Procedure

3-[4-(3-Aminopropyl)-1,2,5-oxadiazol-3-yl]-4-(3-chloro-4-fluorophenyl)-1,2,4-oxadiazol-5(4H)-one trifluoroacetate (7.8 mg, 0.017 mmol) and sulfamide (9.4 mg, 0.98 mol) was dissolved in pyridine (1.0 mL). The solution was heated at 120° C. for 3 minutes in a microwave. A solution of sodium hydroxide in water (0.5 mL, 1.0 N) was added and the mixture stirred at room temperature for 16 hrs. Acidification with acetic acid and purification by preparative LCMS gave the desired product (5.7 mg, 84%). 1H NMR (400 MHz, CD3OD): δ 7.02 (t, 1H), 6.95 (m, 1H), 6.7 (m, 1H), 3.1 (m, 2H), 2.9 (m, 2H), 2.0 (m, 2H). MF═C12H14ClFN6O4S. LCMS calculated for C12H15ClFN6O4S(M+H)+: m/z=393.0.

Workup

customAcidification with acetic acid and purification by preparative LCMS

Sources & evidence

ORD record: ord-32c55c5883274c0694e0abc7613f7022
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08450351B2

Reaction notes

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