m-Chloroperbenzoic acid → 4-(2-(3(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-ylcarbamoyl)imidazo[1,2-a]pyridin-7-yloxy)ethyl)-1-methylpiperazine 1-oxide

HRID 79337Notes

Reaction equation

[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[NH:12][C:13]([C:15]2[N:19]3[CH:20]=[CH:21][C:22]([O:24][CH2:25][CH2:26][N:27]4[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]4)=[CH:23][C:18]3=[N:17][CH:16]=2)=[O:14])[N:5]([CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([CH3:41])[N:36]=2)[N:4]=1)[CH3:2].ClC1C=CC=C(C(OO)=[O:50])C=1>C(Cl)Cl>[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[NH:12][C:13]([C:15]2[N:19]3[CH:20]=[CH:21][C:22]([O:24][CH2:25][CH2:26][N:27]4[CH2:28][CH2:29][N+:30]([O-:50])([CH3:33])[CH2:31][CH2:32]4)=[CH:23][C:18]3=[N:17][CH:16]=2)=[O:14])[N:5]([CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([CH3:41])[N:36]=2)[N:4]=1)[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-7-(2-(4-methylpiperazin-1-yl)ethoxy)imidazo[1,2-a]pyridine-3-carboxamide (25 mg, 0.045 mmol; prepared according to Example 45) in DCM (3 mL) at 0° C. was added metachloroperbenzoic acid (7.8 mg, 0.032 mmol). The reaction mixture was stirred at 0° C. for one hour. The reaction mixture was concentrated under reduced pressure and silica gel chromatography (DCM/MeOH/NH4OH 10:1:0.1) provided the final product (10 mg). MS (ES+APCI) m/z=569 (M+H).

Workup

concentrationThe reaction mixture was concentrated under reduced pressure and silica gel chromatography (DCM/MeOH/NH4OH 10:1:0.1)

Sources & evidence

ORD record: ord-f445c89201564ed8a0430c5aa51c6db7
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841455B2

Reaction notes

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