Hydrochloric Acid → HCID 24863585, compound

HRID 2092296Notes

Reaction equation

[CH3:1][C:2]1([CH3:38])[C:10]2[C:5](=[CH:6][C:7]([NH:11][C:12]3[C:21]4[C:16](=[C:17]([C:23]5[CH:24]=[C:25]6[C:30](=[CH:31][CH:32]=5)[N:29]=[C:28]([NH:33][CH3:34])[N:27]=[CH:26]6)[C:18]([CH3:22])=[CH:19][CH:20]=4)[CH:15]=[CH:14][N:13]=3)=[CH:8][CH:9]=2)[N:4](C(=O)C)[CH2:3]1.Cl>CCO>[CH3:1][C:2]1([CH3:38])[C:10]2[C:5](=[CH:6][C:7]([NH:11][C:12]3[C:21]4[C:16](=[C:17]([C:23]5[CH:24]=[C:25]6[C:30](=[CH:31][CH:32]=5)[N:29]=[C:28]([NH:33][CH3:34])[N:27]=[CH:26]6)[C:18]([CH3:22])=[CH:19][CH:20]=4)[CH:15]=[CH:14][N:13]=3)=[CH:8][CH:9]=2)[NH:4][CH2:3]1

Participants

Conditions

Temperature: 50 °C

Procedure

1-(3,3-Dimethyl-6-(6-methyl-5-(2-(methylamino)quinazolin-6-yl)isoquinolin-1-ylamino)indolin-1-yl)ethanone (180 mg, 0.36 mmol) was dissolved in 5 mL of EtOH and treated with 2 mL of concentrated aqueous HCl. The mixture was heated to 50° C. for 6 h. The mixture was concentrated and the residue was taken up in DCM and neutralized with 2 M ammonia in MeOH. The solution was pre-adsorbed onto silica gel and purified by column chromatography on silica gel using a gradient of 3 to 12% of MeOH in DCM. The clean fraction were concentrated under vacuum and the residue triturated with 1:1 diethyl ether/hexane to give 120 mg of 6-(1-(3,3-dimethylindolin-6-ylamino)-6-methylisoquinolin-5-yl)-N-methylquinazolin-2-amine as a pale yellow solid. MS (M+H)+ 461.

Workup

concentrationThe mixture was concentrated
custompurified by column chromatography on silica gel using a gradient of 3 to 12% of MeOH in DCM
concentrationThe clean fraction were concentrated under vacuum
customthe residue triturated with 1:1 diethyl ether/hexane

Sources & evidence

ORD record: ord-bfb0e16d3ac243808fcf2f88ffe635d7
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08440674B2

Reaction notes

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