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

HRID 271725Notes

Reaction equation

[CH:1]1([CH2:4][NH2:5])[CH2:3][CH2:2]1.CS(O[CH2:11][CH2:12][N:13]1[C:21]2[C:16](=[CH:17][C:18]([C:22]#[C:23][C:24]3[CH:29]=[CH:28][C:27]([C:30]4[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=4)=[CH:26][N:25]=3)=[CH:19][CH:20]=2)[CH:15]=[CH:14]1)(=O)=O>CN(C=O)C>[Cl:36][C:33]1[CH:32]=[CH:31][C:30]([C:27]2[CH:28]=[CH:29][C:24]([C:23]#[C:22][C:18]3[CH:17]=[C:16]4[C:21](=[CH:20][CH:19]=3)[N:13]([CH2:12][CH2:11][NH:5][CH2:4][CH:1]3[CH2:3][CH2:2]3)[CH:14]=[CH:15]4)=[N:25][CH:26]=2)=[CH:35][CH:34]=1

Participants

Conditions

Temperature: 60 °C

Procedure

0.46 mL (5.4 mmol) C-cyclopropyl-methylamine are added to a solution of 2.03 g (4.5 mmol) 2-{5-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-indol-1-yl}-ethyl methanesulphonate in 20 mL DMF and the reaction mixture is stirred for 4 h at 60° C. The mixture is evaporated down i.vac., the residue is stirred with DCM, the precipitate is suction filtered and dried in the air. The product is precipitated as the methanesulphonic acid salt.

Workup

customThe mixture is evaporated down i.vac
stirring, the residue is stirred with DCM
filtrationfiltered
customdried in the air
customThe product is precipitated as the methanesulphonic acid salt

Sources & evidence

ORD record: ord-7f61b68f4f954f1086e34d1df20050df
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07452911B2

Reaction notes

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