Diisopropylethylamine → HCID 70087585, compound

HRID 1250407Notes

Reaction equation

HRID 1250407 reaction equation
N1C=[CH:5][CH:4]=[C:3]([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[C:9]2[C:17]([OH:19])=O)C=1.[C:20]1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[CH:37]([N:40](CC)C(C)C)(C)C.Cl.Cl.[CH3:48][N:49]([CH3:58])[C:50]1[CH:57]=[CH:56][C:53]([CH2:54][NH2:55])=[CH:52][CH:51]=1>CN(C)C=O>[CH3:48][N:49]([CH3:58])[C:50]1[CH:57]=[CH:56][C:53]([CH2:54][NH:55][C:17]([C:9]2[N:8]([C:7]3[CH:37]=[N:40][CH:5]=[CH:4][CH:3]=3)[C:16]3[C:11]([C:10]=2[CH3:20])=[CH:12][CH:13]=[CH:14][CH:15]=3)=[O:19])=[CH:52][CH:51]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 27346334-(aminomethyl)-N,N-dimethylaniline dihydrochlorideHCID 11685290HCID 11685290, compound

Product 1

HCID 70087585HCID 70087585, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

This compound was prepared from 1-(3-pyridyl-methyl)-1H-indole-2-carboxylic acid (200 mg, 0.79 mmol), diphenylphosphoryl azide (222.7 μl, 1.03 mmol), N,N-diisopropylethylamine (364 μl), and 4-dimethylamino-benzylamine dihydrochloride (632.3 mg, 2.84 mmol) in N,N-dimethylformamide (10 ml) as described in example 3/1. The purification by flash chromatography on silica gel was done with toluene/ethyl acetate first 6:1, then going to pure ethyl acetate in two steps: 228.7 mg (76%) of the desired product were obtained. M.p. 108-110° C. MS: 385.3 (M+H+).

Workup

  1. customThe purification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-6bf1954f6b3a4a1ebaf51eaa0a9c2d92
Source dataset
uspto-grants-2002_01
Patent number
US06337344B1

Reaction notes

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