Methanol → HCID 66831591, compound

HRID 58682Notes

Reaction equation

HRID 58682 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]CN.CN(C([O:22][N:23]1N=N[C:25]2[CH:26]=[CH:27]C=N[C:24]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.C[OH:49].[CH3:50][N:51]([CH:53]=[O:54])C>ClCCl>[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][CH2:50][NH:51][C:53]([C:24]1[CH:25]=[C:26]([CH2:27][OH:49])[O:22][N:23]=1)=[O:54]

Participants

7

Reactant 5

HCID 887MethanolHCID 6228DimethylformamideHCID 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 66831591HCID 66831591, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

This compound was prepared following Method A starting from 2-(5-chloro-1H-indol-3-yl)ethanamine hydrochloride (0.500 g; 2.12 mmol), intermediate 5 (0.303 g; 2.12 mmol), HATU (0.887 g; 2.33 mmol) and N,N-diisopropylethylamine (0.699 g; 5.30 mmol) in DMF (5 mL). Flash chromatography on silica gel eluting with 1 to 15% of methanol in dichloromethane gave 0.528 g (78%) of N-(2-(5-chloro-1H-indol-3-yl)ethyl)-5-(hydroxymethyl)isoxazole-3-carboxamide as a solid.

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-3aeb5cbf3c8c486dab19664af1987f72
Source dataset
uspto-grants-2016_09
Patent number
US09434722B2

Reaction notes

Loading…