2,1,3-Benzothiadiazole, 4-chlorosulfonyl- → HCID 11606481, compound

HRID 2265196Notes

Reaction equation

[NH2:1][C:2]1[CH:10]=[C:9]([Br:11])[CH:8]=[C:7]2[C:3]=1[C:4](=[O:22])[N:5]([CH2:13][C@H:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:15])[C:6]2=[O:12].[N:23]1[S:27][N:26]=[C:25]2[C:28]([S:32](Cl)(=[O:34])=[O:33])=[CH:29][CH:30]=[CH:31][C:24]=12>CCOC(C)=O>[Br:11][C:9]1[CH:8]=[C:7]2[C:3]([C:4](=[O:22])[N:5]([CH2:13][C@H:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH3:15])[C:6]2=[O:12])=[C:2]([NH:1][S:32]([C:28]2[C:25]3=[N:26][S:27][N:23]=[C:24]3[CH:31]=[CH:30][CH:29]=2)(=[O:34])=[O:33])[CH:10]=1

Participants

Conditions

Temperature: 170 °C

Procedure

A mixture of (S)-4-amino-6-bromo-2-(2-phenyl-propyl)-isoindole-1,3-dione (30 mg, 0.08 mmol) and benzo[1,2,5]thiadiazole-4-sulfonyl chloride (150 mg, 0.64 mmol) was heated to 170° C. forming a melt and stirred for 2 h. The mixture was allowed to cool, and the solidified residue was dissolved in EtOAc, and the solution was washed with satd. aq. NaHCO3, dried (Na2SO4), and concentrated. Purification by flash chromatography (EtOAc/hexanes) gave the desired sulfonamide as a tan solid (30 mg, 64%). HPLC: RT=11.01 min. MS (ESI−): mass calcd. for C23H17BrN4O4S2, 555.99; m/z found, 555/557 [M−H]−. 1H NMR (400 MHz, CDCl3): 9.59 (br s, 1H), 8.39 (dd, J=7.0, 1.0, 1H), 8.27 (dd, J=8.8, 1.0, 1H), 8.08 (d, J=1.4, 1H), 7.75 (dd, J=8.8, 7.1, 1H), 7.47 (d, J=1.3, 1H), 7.27-7.22 (m, 2H), 7.21-7.17 (m, 3H), 3.78 (dd, J=13.6, 8.1, 1H), 3.68 (dd, J=13.6, 7.81, 1H), 3.26 (sextet, J=7.4, 1H), 1.26 (d, J=7.0, 3H).

Workup

customforming a melt
temperatureto cool
washthe solution was washed with satd
dry with materialaq. NaHCO3, dried (Na2SO4)
concentrationconcentrated
customPurification by flash chromatography (EtOAc/hexanes)

Sources & evidence

ORD record: ord-2ed37158c7ca43599f090f54515a1f8b
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07855292B2

Reaction notes

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