Diisopropylethylamine → HCID 86699441, compound

HRID 1777671Notes

Reaction equation

HRID 1777671 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][CH:18]=1)[O:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=1)C(O)=O.Cl.[Cl:20][C:21]1[CH:22]=[C:23]2[C:27](=[CH:28][CH:29]=1)[NH:26][CH:25]=[C:24]2[CH2:30][CH2:31][NH2:32].CN([C:36]([O:40]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:20][C:21]1[CH:22]=[C:23]2[C:27](=[CH:28][CH:29]=1)[NH:26][CH:25]=[C:24]2[CH2:30][CH2:31][NH:32][C:36](=[O:40])[C:13]1[CH:14]=[CH:15][C:7]([O:6][C:5]2[CH:16]=[CH:17][CH:18]=[C:3]([O:2][CH3:1])[CH:4]=2)=[CH:8][CH:9]=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 63942870HCID 63942870, compound

Product 1

HCID 86699441HCID 86699441, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-(2-(5-Chloro-1H-indol-3-yl)ethyl)-4-(3-methoxyphenoxy)benzamide was prepared according to method A with 3-(3-methoxyphenoxy)benzoic acid (0.080 g, 0.347 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 0.040 g (29%) of the title compound as a white solid.

Workup

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

Sources & evidence

ORD record
ord-4a8e7208545449729668476872a99cd6
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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