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

HRID 1916714Notes

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
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-169827c5490b4291ba8f0f26bfe90d6d
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08618132B2

Reaction notes

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