Dimethylformamide → HCID 66831886, compound

HRID 1918679Notes

Reaction equation

HRID 1918679 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].CN(C([O:22][N:23]1N=N[C:25]2[CH:26]=[CH:27][CH:28]=N[C:24]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)[CH:43]([CH3:45])[CH3:44])(C)C.[C:48](OCC)(=[O:50])C.[CH3:54]N(C=O)C>CCCCCCC>[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][NH:14][C:48]([C:24]1[CH:25]=[C:26]([CH:27]2[CH2:28][CH2:44][CH2:43][CH2:45][CH2:54]2)[O:22][N:23]=1)=[O:50]

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 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)

Product 1

HCID 66831886HCID 66831886, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

This compound was prepared following Method A starting from 2-(5-chloro-1H-indol-3-yl)ethanamine hydrochloride (0.100 g; 0.424 mmol), intermediate 20 (5-cyclohexylisoxazole-3-carboxylic acid) (0.087 g; 0.445 mmol), HATU (0.177 g; 0.466 mmol) and N,N-diisopropylethylamine (0.185 mL; 1.06 mmol) in DMF (3 mL). Flash chromatography on silica gel eluting with 7 to 60% of ethyl acetate in heptane gave 0.079 g (50%) of N-(2-(5-chloro-1H-indol-3-yl)ethyl)-5-cyclohexylisoxazole-3-carboxamide as a solid.

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-b5eea97f8102443081b7bd4c010eee22
Source dataset
uspto-grants-2013_12
Patent number
US08618138B2

Reaction notes

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