Trifluoroacetic acid → HCID 68032129, compound

HRID 1808884Notes

Reaction equation

HRID 1808884 reaction equation
[Cl:1][C:2]1[C:7]([N:8]2[CH2:13][CH2:12][N:11](C(C3C(C4C=CC=CC=4OC)=NOC=3C)=O)[CH2:10][CH2:9]2)=[CH:6][C:5]([NH:30][C:31](=[O:43])[C:32]2[CH:37]=[CH:36][C:35]([NH:38][S:39]([CH3:42])(=[O:41])=[O:40])=[CH:34][CH:33]=2)=[C:4]([N+:44]([O-:46])=[O:45])[CH:3]=1.B(Br)(Br)Br.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:1][C:2]1[C:7]([N:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]2)=[CH:6][C:5]([NH:30][C:31](=[O:43])[C:32]2[CH:33]=[CH:34][C:35]([NH:38][S:39]([CH3:42])(=[O:41])=[O:40])=[CH:36][CH:37]=2)=[C:4]([N+:44]([O-:46])=[O:45])[CH:3]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 25134Boron tribromideHCID 66692574HCID 66692574, compound

Product 1

HCID 68032129HCID 68032129, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(4-Chloro-5-(4-(3-(2-methoxyphenyl)-5-methylisoxazole-4-carbonyl)piperazin-1-yl)-2-nitrophenyl)-4-(methylsulfonamido)benzamide was treated with boron tribromide as described in Example 117. The crude product (140 mg) was treated with 0.8 M trifluoroacetic acid in DCM (4.0 mL) at room temperature overnight. Solvent was evaporated in vacuo and the product was purified by preparative HPLC (0.1% TFA MeOH/H2O) to give 53 mg (55% yield) of the title compound. H1-NMR (500 MHz, CD3OD) δ 8.57 (1H, s), 8.36 (1H, s), 7.98 (2H, d, J=8.9 Hz), 7.41 (2H, d, J=8.9 Hz), 3.48-3.53 (4H, m), 3.42-3.48 (4H, m), 3.08 (3H, s).

Workup

  1. customSolvent was evaporated in vacuo
  2. customthe product was purified by preparative HPLC (0.1% TFA MeOH/H2O)

Sources & evidence

ORD record
ord-8071da77223e4ec1aef3c0a890e3e9fc
Source dataset
uspto-grants-2013_01
Patent number
US08362004B2

Reaction notes

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