Sulfamide → N-[3-({4-[4-(3-Bromo-4-fluorophenyl)-5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl]-1,2,5-oxadiazol-3-yl}amino)propyl]sulfamide

HRID 2402209Notes

Reaction equation

HRID 2402209 reaction equation
I.[NH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7]1[C:8]([C:12]2[N:16]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[C:19]([Br:24])[CH:18]=3)[C:15](=[O:25])[O:14][N:13]=2)=[N:9][O:10][N:11]=1.[S:26](N)([NH2:29])(=[O:28])=[O:27]>N1C=CC=CC=1>[Br:24][C:19]1[CH:18]=[C:17]([N:16]2[C:15](=[O:25])[O:14][N:13]=[C:12]2[C:8]2[C:7]([NH:6][CH2:5][CH2:4][CH2:3][NH:2][S:26]([NH2:29])(=[O:28])=[O:27])=[N:11][O:10][N:9]=2)[CH:22]=[CH:21][C:20]=1[F:23]

Participants

4

Reactant 2

HCID 82267SulfamideHCID 666058273-{4-[(3-Aminopropyl)amino]-1,2,5-oxadiazol-3-yl}-4-(3-bromo-4-fluorophenyl)-1,2,4-oxadiazol-5(4H)-one hydroiodide

Product 1

HCID 66605547N-[3-({4-[4-(3-Bromo-4-fluorophenyl)-5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl]-1,2,5-oxadiazol-3-yl}amino)propyl]sulfamideYield 71.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 3-{4-[(3-aminopropyl)amino]-1,2,5-oxadiazol-3-yl}-4-(3-bromo-4-fluorophenyl)-1,2,4-oxadiazol-5(4H)-one hydroiodide (150 mg, 0.28 mmol) and sulfamide (160 mg, 1.7 mmol) in pyridine (2.5 mL) was heated in a microwave at 130° C. for 10 min. The reaction mixture was concentrated to give a crude residue. This material was purified by preparative LCMS to give the desired product (96 mg, 71%) as a solid. LCMS for C13H14BrFN7O5S (M+H)+: m/z=478.0, 480.0. 1H NMR (400 MHz, DMSO-d6): δ 8.07 (dd, J=6.2, 2.5 Hz, 1H), 7.73-7.69 (m, 1H), 7.59 (dd, J=8.8, 8.6 Hz, 1H), 6.57-6.51 (m, 4H), 3.31-3.26 (m, 2H), 2.92-2.87 (m, 2H), 1.79-1.72 (m, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto give a crude residue
  3. customThis material was purified by preparative LCMS

Sources & evidence

ORD record
ord-bfd55784d2d34a6c991d576426d84f62
Source dataset
uspto-grants-2014_08
Patent number
US08796319B2

Reaction notes

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