Diisopropylethylamine → N-(2-(5-fluoro-1H-indol-3-yl)ethyl)-4-methyl-2-p-tolylthiazole-5-carboxamide

HRID 58786Notes

Reaction equation

HRID 58786 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][NH2:13].[CH3:14][C:15]1[N:16]=[C:17]([C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=2)[S:18][C:19]=1[C:20](O)=[O:21].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>CN(C=O)C.ClCCl.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][NH:13][C:20]([C:19]1[S:18][C:17]([C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=2)=[N:16][C:15]=1[CH3:14])=[O:21]

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 1646825-FluorotryptamineHCID 27636254-Methyl-2-(4-methylphenyl)-1,3-thiazole-5-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 17600490N-(2-(5-fluoro-1H-indol-3-yl)ethyl)-4-methyl-2-p-tolylthiazole-5-carboxamideYield 27.2%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

This compound was prepared following Method A starting from 2-(5-fluoro-1H-indol-3-yl)ethanamine (0.030 g; 0.168 mmol), 4-methyl-2-p-tolylthiazole-5-carboxylic acid (0.043 g; 0.185 mmol), HATU (0.070 g; 0.185 mmol) and N,N-diisopropylethylamine (0.78 mL; 0.420 mmol) in DMF (5 mL). Flash chromatography on silica gel eluting with 1 to 5% of ethyl acetate in dichloromethane gave 0.018 g (27%) of N-(2-(5-fluoro-1H-indol-3-yl)ethyl)-4-methyl-2-p-tolylthiazole-5-carboxamide as a solid.

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-894866145c374b209ff66c8c0904ece3
Source dataset
uspto-grants-2016_09
Patent number
US09434722B2

Reaction notes

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