Triethylamine → HCID 66831672, compound

HRID 58679Notes

Reaction equation

HRID 58679 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][CH2:13][NH2:14].[CH2:15]([N:22]1[C:26]([C:27](Cl)=[O:28])=[CH:25][C:24]([C:30]([CH3:33])([CH3:32])[CH3:31])=[N:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(CC)CC)C.C(OCC)(=O)C>ClCCl>[CH2:15]([N:22]1[C:26]([C:27]([NH:14][CH2:13][CH2:12][C:6]2[C:5]3[C:9](=[CH:10][CH:11]=[C:3]([Cl:2])[CH:4]=3)[NH:8][CH:7]=2)=[O:28])=[CH:25][C:24]([C:30]([CH3:33])([CH3:32])[CH3:31])=[N:23]1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 27993221-benzyl-3-tert-butyl-1H-pyrazole-5-carbonyl chlorideHCID 28274945-Chloro-1H-indole-3-ethylamine monohydrochloride

Product 1

HCID 66831672HCID 66831672, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

This compound was obtained following Method B starting from 2-(5-chloro-1H-indol-3-yl)ethanamine hydrochloride (0.0445 g, 0.189 mmol), 1-benzyl-3-(tert-butyl)-1H-pyrazole-5-carbonyl chloride (0.055 g; 0.189 mmol), and triethylamine (0.0663 mL; 0.472 mmol) in dichloromethane (3 mL). Flash chromatography on silica gel eluting with 2 to 16% of ethyl acetate in dichloromethane gave 0.0485 g (59%) of 1-benzyl-3-tert-butyl-N-(2-(5-chloro-1H-indol-3-yl)ethyl)-1H-pyrazole-5-carboxamide as a solid.

Workup

  1. customThis compound was obtained

Sources & evidence

ORD record
ord-4e4bb5a7b55b47ce8ad780a926bc3cdc
Source dataset
uspto-grants-2016_09
Patent number
US09434722B2

Reaction notes

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