Diisopropylethylamine → HCID 66831737, compound

HRID 58715Notes

Reaction equation

HRID 58715 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].[N:15]1([C:20]2[CH:21]=[C:22]([N:26]3[CH2:30][CH2:29][CH:28]([C:31](O)=[O:32])[C:27]3=[O:34])[CH:23]=[CH:24][CH:25]=2)[CH:19]=[CH:18][CH:17]=[CH:16]1.N1(C2C=C(N3CCC(C(O)=O)C3=O)C=CC=2)C=CC=C1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>CN(C=O)C>[N:15]1([C:20]2[CH:21]=[C:22]([N:26]3[CH2:30][CH2:29][CH:28]([C:31]([NH:14][CH2:13][CH2:12][C:6]4[C:5]5[C:9](=[CH:10][CH:11]=[C:3]([Cl:2])[CH:4]=5)[NH:8][CH:7]=4)=[O:32])[C:27]3=[O:34])[CH:23]=[CH:24][CH:25]=2)[CH:19]=[CH:18][CH:17]=[CH:16]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 28274945-Chloro-1H-indole-3-ethylamine monohydrochlorideHCID 66832064HCID 66832064, compound

Product 1

HCID 66831737HCID 66831737, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

This compound was prepared according to method E with 2-(5-chloro-1H-indol-3-yl)ethanamine hydrochloride (0.100 g; 0.433 mmol), 1-(3-(1H-pyrrol-1-yl)phenyl)-2-oxopyrrolidine-3-carboxylic acid 1-(3-(1H-pyrrol-1-yl)phenyl)-2-oxopyrrolidine-3-carboxylic acid (0.117 g; 0.433 mmol), PyBOP (0.225 g; 0.433 mmol), N,N diisopropylethylamine (0.186 mL; 1.08 mmol) in DMF (3 mL). The crude mixture was purified flash chromatography on silica (eluent 20 to 100% ethyl acetate in heptane and 2 to 20% ethyl acetate in dichloromethane) to yield 0.058 g (30%) of 1-(3-(1H-pyrrol-1-yl)phenyl)-N-(2-(5-chloro-1H-indol-3-yl)ethyl)-2-oxopyrrolidine-3-carboxamide as a white solid.

Workup

  1. customThis compound was prepared
  2. customThe crude mixture was purified flash chromatography on silica (eluent 20 to 100% ethyl acetate in heptane and 2 to 20% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-219d230e95b042c8a08045af1de0d815
Source dataset
uspto-grants-2016_09
Patent number
US09434722B2

Reaction notes

Loading…