Cyclopropanemethanamine, N-propyl- → (2-{5-[5-(4-Chloro-phenyl)-pyridin-2-ylethynyl]-indol-1-yl}-ethyl)-cyclopropylmethyl-propyl-amine

HRID 1916713Notes

Reaction equation

[CH:1]1([CH2:4][NH:5][CH2:6][CH2:7][CH3:8])[CH2:3][CH2:2]1.CS(O[CH2:14][CH2:15][N:16]1[C:24]2[C:19](=[CH:20][C:21]([C:25]#[C:26][C:27]3[CH:32]=[CH:31][C:30]([C:33]4[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=4)=[CH:29][N:28]=3)=[CH:22][CH:23]=2)[CH:18]=[CH:17]1)(=O)=O>CN(C=O)C>[Cl:39][C:36]1[CH:35]=[CH:34][C:33]([C:30]2[CH:31]=[CH:32][C:27]([C:26]#[C:25][C:21]3[CH:20]=[C:19]4[C:24](=[CH:23][CH:22]=3)[N:16]([CH2:15][CH2:14][N:5]([CH2:4][CH:1]3[CH2:3][CH2:2]3)[CH2:6][CH2:7][CH3:8])[CH:17]=[CH:18]4)=[N:28][CH:29]=2)=[CH:38][CH:37]=1

Participants

Conditions

Temperature: 60 °C

Procedure

63 μL (0.44 mmol) cyclopropylmethyl-propyl-amine are added to a solution of 100 mg (0.22 mmol) 2-{5-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-indol-1-yl}-ethyl methanesulphonate in 2 mL DMF and the reaction mixture is stirred for 16 h at 60° C. The mixture is evaporated down i. vac., the residue is taken up in DCM, the organic phase is washed with water and dilute K2CO3 solution and dried over Na2SO4. After the desiccant and solvent have been eliminated the residue is purified twice by chromatography (Alox, cyc/EtOAc 8:2 and cyc/DCM 1:1).

Workup

customThe mixture is evaporated down i
washthe organic phase is washed with water and dilute K2CO3 solution
dry with materialdried over Na2SO4
customis purified twice by chromatography (Alox, cyc/EtOAc 8:2 and cyc/DCM 1:1)

Sources & evidence

ORD record: ord-2d02db9d770249e3a9cffc7753d750c6
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08618132B2

Reaction notes

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