Hydrochloric Acid → Alectinib Hydrochloride

HRID 2202445Notes

Reaction equation

HRID 2202445 reaction equation
[CH2:1]([C:3]1[C:24]([N:25]2[CH2:30][CH2:29][CH:28]([N:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)[CH2:27][CH2:26]2)=[CH:23][C:6]2[C:7]([CH3:22])([CH3:21])[C:8]3[NH:9][C:10]4[C:15]([C:16]=3[C:17](=[O:18])[C:5]=2[CH:4]=1)=[CH:14][CH:13]=[C:12]([C:19]#[N:20])[CH:11]=4)[CH3:2].[ClH:37].C(O)C>C(C(C)=O)C.O.C(O)(=O)C>[ClH:37].[CH2:1]([C:3]1[C:24]([N:25]2[CH2:30][CH2:29][CH:28]([N:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)[CH2:27][CH2:26]2)=[CH:23][C:6]2[C:7]([CH3:22])([CH3:21])[C:8]3[NH:9][C:10]4[C:15]([C:16]=3[C:17](=[O:18])[C:5]=2[CH:4]=1)=[CH:14][CH:13]=[C:12]([C:19]#[N:20])[CH:11]=4)[CH3:2]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 49806720Alectinib

Product 1

HCID 53239799Alectinib Hydrochloride

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
60 °C

Procedure

9-Ethyl-6,6-dimethyl-8-(4-morpholin-4-yl-piperidin-1-yl)-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile was dissolved in a mixture of 10 v/w of methyl ethyl ketone, 4 v/w of water, and 3 v/w of acetic acid at 60° C. To the dissolved solution, 1 v/w of hydrochloric acid (2 N) was added dropwise. After stirring at 60° C. for 30 minutes, 25 v/w of ethanol was added dropwise. The precipitated solid was filtered and dried to give 9-ethyl-6,6-dimethyl-8-(4-morpholin-4-yl-piperidin-1-yl)-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile monohydrochloride salt. 9-Ethyl-6,6-dimethyl-8-(4-morpholin-4-yl-piperidin-1-yl)-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile monohydrochloride salt obtained was pulverized by using a jet mill.

Workup

  1. filtrationThe precipitated solid was filtered
  2. customdried

Sources & evidence

ORD record
ord-cd66312c138b46f2951aee25d0e2933e
Source dataset
uspto-grants-2016_06
Patent number
US09365514B2

Reaction notes

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