Boron tribromide → 3-[[7-(2-Chloro-5-hydroxyphenyl)-5-methyl-1,2,4-benzotriazin-3-yl]amino]-N-[2-(dimethylamino)ethyl]benzenesulfonamide

HRID 273500Notes

Reaction equation

HRID 273500 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8]C)=[CH:4][C:3]=1[C:10]1[CH:35]=[C:34]([CH3:36])[C:13]2[N:14]=[C:15]([NH:18][C:19]3[CH:20]=[C:21]([S:25]([NH:28][CH2:29][CH2:30][N:31]([CH3:33])[CH3:32])(=[O:27])=[O:26])[CH:22]=[CH:23][CH:24]=3)[N:16]=[N:17][C:12]=2[CH:11]=1.B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[C:10]1[CH:35]=[C:34]([CH3:36])[C:13]2[N:14]=[C:15]([NH:18][C:19]3[CH:20]=[C:21]([S:25]([NH:28][CH2:29][CH2:30][N:31]([CH3:33])[CH3:32])(=[O:26])=[O:27])[CH:22]=[CH:23][CH:24]=3)[N:16]=[N:17][C:12]=2[CH:11]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 59837591HCID 59837591, compound

Product 1

HCID 116492143-[[7-(2-Chloro-5-hydroxyphenyl)-5-methyl-1,2,4-benzotriazin-3-yl]amino]-N-[2-(dimethylamino)ethyl]benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-[7-(2-chloro-5-methoxy-phenyl)-5-methyl-benzo[1,2,4]triazin-3-ylamino]-N-(2-dimethylamino-ethyl)-benzenesulfonamide (0.32 mmol, 1.0 equiv) was dissolved in 10 mL of anhydrous DCM and placed under an argon atmosphere. 4 mL of BBr3 (0.1 M) added via syringe and the reaction stirred at room temperature for 2 h. BBr3 was quenched with saturated NaHCO3 until pH=7. The mixture was filtered and washed with water and Et2O to give 3-[7-(2-chloro-5-hydroxy-phenyl)-5-methyl-benzo[1,2,4]triazin-3-ylamino]-N-(2-dimethylamino-ethyl)-benzenesulfonamide, as an orange solid (132.2 mg, 81% yield). 1H NMR (DMSO-d6): δ 2.71 (s, 2H), 3.01 (bs, 2H), 6.87 (dd, J=8.8 Hz, J=2.9 Hz, 1H), 6.94 (d, J=3.0 Hz, 1H), 7.41 (d, J=8.8 Hz, 1H), 7.51 (d, J=7.9 Hz, 1H), 7.64 (t, J=8.1 Hz, 2H), 7.90 (s, 1H), 8.06 (d, J=6.7 Hz, 1H), 8.20 (s, 1H), 8.89 (s, 1H), 9.93 (s, 1H), 11.34 (s, 1H). MS (ES+) m/z=513. LC retention time 2.24 min.

Workup

  1. customBBr3 was quenched with saturated NaHCO3 until pH=7
  2. filtrationThe mixture was filtered
  3. washwashed with water and Et2O

Sources & evidence

ORD record
ord-f93e8beb49c146eb8bb4ba325c20909a
Source dataset
uspto-grants-2008_11
Patent number
US07456176B2

Reaction notes

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