Sodium Hydroxide → HCID 178514780, compound

HRID 1845791Notes

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-afc39489c80e4a8da91d6d7a2dc17f4b
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08951536B2

Reaction notes

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