Trifluoroacetic acid → HCID 178464828, compound

HRID 2053962Notes

Reaction equation

HRID 2053962 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](O)=[O:5].[CH2:26]([NH:28][CH:29]1[CH2:34][CH2:33][N:32](C(OC(C)(C)C)=O)[CH2:31][CH2:30]1)[CH3:27].C(N(C(C)C)CC)(C)C.FC(F)(F)C(O)=O.ClCl>CS(C)=O>[Cl:1][C:2]1[CH:10]=[C:9]([CH:8]=[CH:7][C:3]=1[C:4]([N:28]([CH2:26][CH3:27])[CH:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)=[O:5])[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

7

Reactant 5

HCID 6422Trifluoroacetic acidHCID 24526ChlorineHCID 81531DiisopropylethylamineHCID 18374730tert-Butyl 4-(ethylamino)piperidine-1-carboxylateHCID 178464831HCID 178464831, compound

Product 1

HCID 178464828HCID 178464828, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Prepared analogously to Example 1d from 2-chloro-4-{N-[1-(5-chloro-1H-benzimidazol-2-yl)ethyl]aminocarbonyl}benzoic acid, tert-butyl 4-ethylaminopiperidin-1-ylcarboxylate, PFTU, and diisopropylethylamine in DMSO at ambient temperature and subsequent reaction with trifluoroacetic acid analogously to Example 17. HPLC-MS results: retention time: 3.87 minutes; C24H27Cl2N5O2 (488.42); mass spectrum: (M−H)−=487/489/491 (chlorine isotope).

Workup

  1. customHPLC-MS results

Sources & evidence

ORD record
ord-3211761523654d54864e8a13cd61ca0d
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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