m-Chloroperbenzoic acid → (5-Benzenesulfinylmethyl-pyrrolo[2,1-f][1,2,4]triazin-4-yl)-[3-chloro-4-(3-fluoro-benzyloxy)-phenyl]-amine

HRID 1829916Notes

Reaction equation

HRID 1829916 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:17][C:18]2[C:23]3=[C:24]([CH2:27][S:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[CH:25]=[CH:26][N:22]3[N:21]=[CH:20][N:19]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1.ClC1C=CC=C(C(OO)=[O:43])C=1>C(Cl)(Cl)Cl>[C:29]1([S:28]([CH2:27][C:24]2[CH:25]=[CH:26][N:22]3[C:23]=2[C:18]([NH:17][C:4]2[CH:5]=[CH:6][C:7]([O:8][CH2:9][C:10]4[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=4)=[C:2]([Cl:1])[CH:3]=2)=[N:19][CH:20]=[N:21]3)=[O:43])[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 22055272[3-Chloro-4-(3-fluoro-benzyloxy)-phenyl]-(5-phenylsulfanylmethyl-pyrrolo[2,1-f][1,2,4]triazin-4-yl)-amine

Product 1

HCID 22055282(5-Benzenesulfinylmethyl-pyrrolo[2,1-f][1,2,4]triazin-4-yl)-[3-chloro-4-(3-fluoro-benzyloxy)-phenyl]-amineYield 90%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The sulfide 7A (900 mg, 1.63 mmol) was dissolved in chloroform (25 ml), cooled in an ice bath and m-chloroperbenzoic acid (300 mg, 57 to 80%, about 1 equiv) was added in small portions over 15 min. After 1 hr., the reaction was washed with 10% aqueous NaHSO3 solution, sat. aq. NaHCO3 solution (three times) and dried (Na2SO4). Removal of the solvent afforded 7B (740 mg, 90%) as a foam. Analytical HPLC retention time=1.99 min. (YMC Xterra S7 C18, 3.0×50 mm column, 10–90% aqueous methanol over 2 minutes containing 0.1% TFA, 5 mL/min, monitoring at 220 nm) and a LC/MS M++1=506.

Workup

  1. temperaturecooled in an ice bath
  2. wash, the reaction was washed with 10% aqueous NaHSO3 solution, sat. aq. NaHCO3 solution (three times)
  3. dry with materialdried (Na2SO4)
  4. customRemoval of the solvent

Sources & evidence

ORD record
ord-c9561f3af9324f9f97233f8379087fcd
Source dataset
uspto-grants-2006_06
Patent number
US07064203B2

Reaction notes

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