Benzylamine → HCID 69780616, compound

HRID 1250392Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][CH:21]=1)[CH2:6][N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[C:8]1[C:16]([OH:18])=[O:17])#[N:2].[CH2:22]([NH2:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C1(P([N:44]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C(N(C(C)C)CC)(C)C>>[C:16]([OH:18])(=[O:17])[CH3:8].[CH2:22]([NH:29][C:16]([C:8]1[N:7]([CH2:6][C:5]2[CH:19]=[CH:20][CH:21]=[C:3]([C:1](=[NH:44])[NH2:2])[CH:4]=2)[C:15]2[C:10]([CH:9]=1)=[CH:11][CH:12]=[CH:13][CH:14]=2)=[O:18])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

Reactant 4

HCID 7504Benzylamine

HCID 81531Diisopropylethylamine

HCID 199401P,P-Diphenylphosphinic azide

HCID 10891118HCID 10891118, compound

Product 1

HCID 69780616HCID 69780616, compoundYield 97%

Procedure

This compound was prepared from 1-(3-cyano-benzyl)-1H-indole-2-carboxylic acid (example 1/2) and benzylamine by using diphenylphosphoryl azide and diisopropylethylamine as described in example 3/1. The crude material was purified by flash chromatography on silica gel with toluene/ethanol 19:0.5 to give the desired product in 97% yield. M.p. 129-131° C. MS: 366.2 (M+H+).

Workup

customThe crude material was purified by flash chromatography on silica gel with toluene/ethanol 19:0.5

Sources & evidence

ORD record: ord-1d84b32fed3a48d0be3f5333b3aea024
Source dataset: uspto-grants-2002_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06337344B1

Reaction notes

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