(+-)-Anabasine → HCID 178464795, compound

HRID 2053977Notes

Reaction equation

HRID 2053977 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([C:11]([NH:13][CH:14]([C:16]2[NH:20][C:19]3[CH:21]=[CH:22][C:23]([Cl:25])=[CH:24][C:18]=3[N:17]=2)[CH3:15])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[N:26]1[CH:31]=[CH:30][CH:29]=[C:28]([CH:32]2[CH2:37][CH2:36][CH2:35][CH2:34][NH:33]2)[CH:27]=1.C(N(C(C)C)CC)(C)C.ClCl>CS(C)=O>[Cl:1][C:2]1[CH:10]=[C:9]([CH:8]=[CH:7][C:3]=1[C:4]([N:33]1[CH2:34][CH2:35][CH2:36][CH2:37][CH:32]1[C:28]1[CH:27]=[N:26][CH:31]=[CH:30][CH:29]=1)=[O:6])[C:11]([NH:13][CH:14]([C:16]1[NH:20][C:19]2[CH:21]=[CH:22][C:23]([Cl:25])=[CH:24][C:18]=2[N:17]=1)[CH3:15])=[O:12]

Participants

6

Reactant 4

HCID 2181(+-)-AnabasineHCID 24526ChlorineHCID 81531DiisopropylethylamineHCID 178464831HCID 178464831, compound

Product 1

HCID 178464795HCID 178464795, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Prepared analogously to Example 1d from rac.-2-chloro-4-{N-[1-(5-chloro-1H-benzimidazol-2-yl)ethyl]aminocarbonyl}benzoic acid, rac.-2-(pyridin-3-yl)piperidine, PFTU, and diisopropylethylamine in DMSO at ambient temperature. HPLC-MS results: retention time: 3.99 minutes; C27H25Cl2N5O2 (522.43); mass spectrum: (M−H)−=521/523/525 (chlorine isotope).

Workup

  1. customHPLC-MS results

Sources & evidence

ORD record
ord-73a224f54fc347cd965a6c334f296cc8
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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