Boron tribromide → 4-Chloro-3-{5-methyl-3-[3-(4-methyl-piperazine-1-sulfonyl)-phenylamino]-benzo[1,2,4]triazin-7-yl}-phenol

HRID 273508Notes

Reaction equation

HRID 273508 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:36]=[C:35]([CH3:37])[C:13]2[N:14]=[C:15]([NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([S:25]([N:28]4[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]4)(=[O:27])=[O:26])[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:36]=[C:35]([CH3:37])[C:13]2[N:14]=[C:15]([NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([S:25]([N:28]4[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]4)(=[O:26])=[O:27])[CH:20]=3)[N:16]=[N:17][C:12]=2[CH:11]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 59837628[7-(2-Chloro-5-methoxy-phenyl)-5-methyl-benzo[1,2,4]triazin-3-yl]-[3-(4-methyl-piperazine-1-sulfonyl)-phenyl]-amine

Product 1

HCID 116350474-Chloro-3-{5-methyl-3-[3-(4-methyl-piperazine-1-sulfonyl)-phenylamino]-benzo[1,2,4]triazin-7-yl}-phenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[7-(2-chloro-5-methoxy-phenyl)-5-methyl-benzo[1,2,4]triazin-3-yl]-[3-(4-methyl-piperazine-1-sulfonyl)-phenyl]-amine (0.0742 mmol, 1.0 equiv) was dissolved in 5 mL anhydrous DCM and placed under an argon atmosphere. 200 mL of BBr3 (0.1 M) was added via syringe to the amine solution and stirred at room temperature for 2 h. BBr3 was quenched with saturated NaHCO3 until pH was adjusted to 7. The mixture was filtered and rinsed with water and Et2O to give 4-chloro-3-{5-methyl-3-[3-(4-methyl-piperazine-1-sulfonyl)-phenylamino]-benzo[1,2,4]triazin-7-yl}-phenol, as a tan solid (24.3 mg, 62% yield). 1H NMR (DMSO-d6): δ 2.71 (s, 6H), 2.72 (bs, 2H), 3.16 (m, 2H), 3.46 (m, 2H), 3.78 (m, 2H), 6.88 (dd, J=8.8 Hz, J=2.9 Hz, 1H), 6.95 (d, J=2.9 Hz, 1H), 7.41 (d, J=8.7 Hz, 1H), 7.45 (dd, J=7.9 Hz, J=1.7 Hz, 1H), 7.72 (t, J=8.1 Hz, 2H), 7.91 (d, J=1.7 Hz, 1H), 8.12 (dd, J=8.3 Hz, J=1.7 Hz, 1H), 8.21 (d, J=1.9 Hz, 1H), 8.93 (d, J=1.9 Hz, 1H), 9.99 (s, 1H), 11.46 (s, 1H). MS(ES+): m/z=526. Elemental for C25H36Cl2N6O8S 5H2O Calculated: C, 46.08; H, 5.57; N, 12.90. Found: C, 46.84; H, 5.04; N, 12.66.

Workup

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

Sources & evidence

ORD record
ord-64cac3b997334c0ebb109f43422b48eb
Source dataset
uspto-grants-2008_11
Patent number
US07456176B2

Reaction notes

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