m-Chloroperbenzoic acid → HCID 20802921, compound

HRID 1072074Notes

Reaction equation

HRID 1072074 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:32]=[CH:33][CH:34]=1)[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([NH:15][C:16]3[C:21]4=[C:22]([CH2:25][N:26]5[CH2:31][CH2:30][S:29][CH2:28][CH2:27]5)[CH:23]=[CH:24][N:20]4[N:19]=[CH:18][N:17]=3)=[CH:12][CH:13]=2)[CH:8]=[N:7]1.ClC1C=CC=C(C(OO)=[O:43])C=1>C(Cl)(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:32]=[CH:33][CH:34]=1)[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([NH:15][C:16]3[C:21]4=[C:22]([CH2:25][N:26]5[CH2:27][CH2:28][S:29](=[O:43])[CH2:30][CH2:31]5)[CH:23]=[CH:24][N:20]4[N:19]=[CH:18][N:17]=3)=[CH:12][CH:13]=2)[CH:8]=[N:7]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 22390523HCID 22390523, compound

Product 1

HCID 20802921HCID 20802921, compoundYield 27.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of [1-(3-fluoro-benzyl)-1H-indazol-5-yl]-[5-(thiomorpholin-4-ylmethyl)-pyrrolo[2,1-f][1,2,4]triazin-4-yl]-amine (46 mg, 0.096 mmole) in chloroform (2 mL) was cooled in an ice bath and m-chloroperbenzoic acid (26 mg, 65%, 1 equiv) was added in portions over 12 min. After 1 hr, the reaction was then diluted with chloroform, washed with 6% aq. NaHSO3 solution, sat. aq. NaHCO3 solution and dried (Na2SO4). The solvent was removed and purification by radial chromatography (2 mm silica gel plate employing gradient elution with DCM containing 0 to 5% MeOH) afforded the title compound as an oil (13 mg, 27%). MS: 490 (M+H)+; HPLC Ret Time: 1.62 min (YMC S5 C18, 4.60×50 mm column, 3 min gradient, 4 mL/min).

Workup

  1. washwashed with 6% aq. NaHSO3 solution, sat. aq. NaHCO3 solution
  2. dry with materialdried (Na2SO4)
  3. customThe solvent was removed
  4. custompurification
  5. washby radial chromatography (2 mm silica gel plate employing gradient elution with DCM containing 0 to 5% MeOH)

Sources & evidence

ORD record
ord-1786936ad7f84f5abf8b77823a26b9af
Source dataset
uspto-grants-2005_06
Patent number
US06908916B2

Reaction notes

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