Diisopropylethylamine → HCID 86699442, compound

HRID 1777672Notes

Reaction equation

HRID 1777672 reaction equation
[C:1]1([CH3:17])[CH:6]=[CH:5][CH:4]=[C:3]([O:7][C:8]2[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=2)C(O)=O)[CH:2]=1.Cl.[Cl:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[NH:25][CH:24]=[C:23]2[CH2:29][CH2:30][NH2:31].CN([C:35]([O:39]N1N=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>[Cl:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[NH:25][CH:24]=[C:23]2[CH2:29][CH2:30][NH:31][C:35](=[O:39])[C:14]1[CH:15]=[CH:16][C:8]([O:7][C:3]2[CH:2]=[C:1]([CH3:17])[CH:6]=[CH:5][CH:4]=2)=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 28274945-Chloro-1H-indole-3-ethylamine monohydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 216628243-(3-Methylphenoxy)benzoic acid

Product 1

HCID 86699442HCID 86699442, compoundYield 35.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-(2-(5-Chloro-1H-indol-3-yl)ethyl)-4-(m-tolyloxy)benzamide was prepared according to method A with 3-(m-tolyloxy)benzoic acid (0.080 g, 0.35 mmol), 2-(5-chloro-1H-indol-3-yl)ethanamine hydrochloride (0.077 g; 0.331 mmol), HATU (0.190 g; 0.365 mmol) and N,N-diisopropylethylamine (0.142 mL; 0.829 mmol) in DMF (3 mL). Flash chromatography on silica gel (eluent 20 to 100% ethyl acetate in heptane) furnished 0.047 g (33%) of the title compound as a white solid.

Workup

  1. customN-(2-(5-Chloro-1H-indol-3-yl)ethyl)-4-(m-tolyloxy)benzamide was prepared

Sources & evidence

ORD record
ord-2144c6918457413ea824318fff7ec236
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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