Boron tribromide → 4-(7-(2-chloro-5-hydroxyphenyl)-5-methylbenzo[e][1,2,4]triazin-3-ylamino)-N-methyl-N-(2-(pyrrolidin-1-yl)ethyl)benzenesulfonamide

HRID 273502Notes

Reaction equation

HRID 273502 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:38]=[C:37]([CH3:39])[C:13]2[N:14]=[C:15]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([S:25]([N:28]([CH3:36])[CH2:29][CH2:30][N:31]4[CH2:35][CH2:34][CH2:33][CH2:32]4)(=[O:27])=[O:26])=[CH:21][CH:20]=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:38]=[C:37]([CH3:39])[C:13]2[N:14]=[C:15]([NH:18][C:19]3[CH:20]=[CH:21][C:22]([S:25]([N:28]([CH3:36])[CH2:29][CH2:30][N:31]4[CH2:32][CH2:33][CH2:34][CH2:35]4)(=[O:26])=[O:27])=[CH:23][CH:24]=3)[N:16]=[N:17][C:12]=2[CH:11]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 598376744-[7-(2-chloro-5-methoxy-phenyl)-5-methyl-benzo[1,2,4]triazin-3-ylamino]-N-methyl-N-(2-pyrrolidin-1-yl-ethyl)-benzenesulfonamide

Product 1

HCID 115268724-(7-(2-chloro-5-hydroxyphenyl)-5-methylbenzo[e][1,2,4]triazin-3-ylamino)-N-methyl-N-(2-(pyrrolidin-1-yl)ethyl)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-[7-(2-chloro-5-methoxy-phenyl)-5-methyl-benzo[1,2,4]triazin-3-ylamino]-N-methyl-N-(2-pyrrolidin-1-yl-ethyl)-benzenesulfonamide (0.297 mmol, 1.0 equiv) was dissolved in 10 mL anhydrous DCM and placed under an argon atmosphere. 4 mL of BBr3 (0.1 M) was added via syringe and the reaction was 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 4-[7-(2-chloro-5-hydroxy-phenyl)-5-methyl-benzo[1,2,4]triazin-3-ylamino]-N-methyl-N-(2-pyrrolidin-1-yl-ethyl)-benzenesulfonamide, as a dark green solid (120.5 mg, 74% yield). Rf=0.61 1H NMR (DMSO-d6): δ 1.90(m, 2H), 2.01 (m, 2H), 2.72 (s, 6H), 3.06 (m, 2H), 3.30 (t, J=5.6 Hz, 2H), 3.38 (t, J=6.0 Hz, 2H), 3.59 (m, 2H), 6.89 (dd, J=8.8 Hz, J=2.9 Hz, 1H), 6.96 (d, J=2.9 Hz, 1H), 7.40 (d, J=8.6 Hz, 1H), 7.87 (d, J=8.9 Hz, 2H), 7.92 (d, J=0.9 Hz, 1H), 8.21 (d, J=1.7 Hz, 1H), 8.30 (d, J=9.0 Hz, H), 11.50 (s, 1H). MS (ES+) m/z=553 LC retention time 2.41 min. Elemental for C27H30Cl2N6O3S 5H2O Calculated: C, 47.72; H, 5.93; N, 11.37. Found: C, 46.59; H, 5.67; N, 11.42.

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-b5eabbb64ea04317825c28c5b47869fa
Source dataset
uspto-grants-2008_11
Patent number
US07456176B2

Reaction notes

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