Methanol → HCID 54765085, compound

HRID 85068Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[C:18]4[C:13](=[N:14][CH:15]=[C:16]([C:19]5[CH:24]=[CH:23][C:22]([CH2:25][N:26]6[CH2:31][CH2:30][NH:29][CH:28]([CH3:32])[CH2:27]6)=[CH:21][CH:20]=5)[CH:17]=4)[N:12](S(C4C=CC(C)=CC=4)(=O)=O)[CH:11]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.CO.C(N(CC)CC)C.[C:52](OC(=O)C)(=[O:54])[CH3:53]>ClCCl>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[C:18]4[C:13](=[N:14][CH:15]=[C:16]([C:19]5[CH:20]=[CH:21][C:22]([CH2:25][N:26]6[CH2:31][CH2:30][N:29]([C:52](=[O:54])[CH3:53])[CH:28]([CH3:32])[CH2:27]6)=[CH:23][CH:24]=5)[CH:17]=4)[NH:12][CH:11]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

Conditions

Temperature: 50 °C

Procedure

3-(1H-indol-5-yl)-5-(4-((3-methylpiperazin-1-yl)methyl)phenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (50 mg) was suspended in 1 mL dichloromethane and 1 mL of methanol and treated with triethylamine (100 mL) and acetic anhydride (20 μL) and stirred for one hour. The mixture was concentrated in vacuo, taken up in EtOAc and washed with water and brine and dried over MgSO4. The residue was suspended in methanol and treated with 5 N NaOH and heated at 50° C. for one hour. The mixture was diluted with dichloromethane and washed with water and brine, dried over MgSO4 and purified by MPLC silica gel chromatography (0-20% MeOH in DCM) to yield an analytical sample (464 M+H).

Workup

concentrationThe mixture was concentrated in vacuo
washwashed with water and brine
dry with materialdried over MgSO4
additiontreated with 5 N NaOH
additionThe mixture was diluted with dichloromethane
washwashed with water and brine
dry with materialdried over MgSO4
custompurified by MPLC silica gel chromatography (0-20% MeOH in DCM)
customto yield an analytical sample (464 M+H)

Sources & evidence

ORD record: ord-2986b35b81884073bd0d027f7f667383
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846909B2

Reaction notes

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