Diisopropylethylamine → 5-Chloro-6-[2-(isopropylamino-methyl)-pyrrolidin-1-yl]-1-methyl-3-naphthalen-2-yl-1H-[4,4']bipyridinyl-2-one

HRID 1795465Notes

Reaction equation

[Cl:1][C:2]1[C:3]([C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)=[C:4]([C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=2)[C:5](=[O:10])[N:6]([CH3:9])[C:7]=1Cl.C(N(C(C)C)CC)(C)C.[CH:36]([NH:39][CH2:40][CH:41]1[CH2:45][CH2:44][CH2:43][NH:42]1)([CH3:38])[CH3:37]>C(Cl)Cl>[Cl:1][C:2]1[C:3]([C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)=[C:4]([C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=2)[C:5](=[O:10])[N:6]([CH3:9])[C:7]=1[N:42]1[CH2:43][CH2:44][CH2:45][CH:41]1[CH2:40][NH:39][CH:36]([CH3:38])[CH3:37]

Participants

Conditions

Temperature: 150 °C

Procedure

A microwave tube was charged with 5,6-dichloro-1-methyl-3-naphthalen-2-yl-1H-[4,4′]bipyridinyl-2-one (0.300 g, 0.8 mmol), diisopropylethylamine (2 eq.) and isopropyl-pyrrolidin-2-ylmethyl-amine (1 eq). The heterogeneous suspension was heated in the microwave at 150° C. for 10 min. The resulting brownish suspension was dissolved in DCM and the crude product was purified by flash chromatography using an ISCO combiflash system with a mixture 97/3 DCM/MeOH to give the title compound. MS (ES+): 487 (M+H)+.

Workup

customthe crude product was purified by flash chromatography

Sources & evidence

ORD record: ord-14ed54ecb4bf4ace808aed17734668e4
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07026326B2

Reaction notes

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