Isonicotinic Acid → 3-[4-[2-(1-Pyrrolidinyl)ethoxy]benzyl]-2-[4-[2-(4-pyridinylcarbonylamino)ethyl]phenyl]benzo[b]thiophene

HRID 1937194Notes

Reaction equation

HRID 1937194 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:14][C:13]3[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=3[C:11]=2[CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][N:29]3[CH2:33][CH2:32][CH2:31][CH2:30]3)=[CH:22][CH:21]=2)=[CH:6][CH:5]=1.[C:34](O)(=[O:41])[C:35]1[CH:40]=[CH:39][N:38]=[CH:37][CH:36]=1.C1CCC(N=C=NC2CCCCC2)CC1>ClCCl>[N:29]1([CH2:28][CH2:27][O:26][C:23]2[CH:22]=[CH:21][C:20]([CH2:19][C:11]3[C:12]4[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=4[S:14][C:10]=3[C:7]3[CH:8]=[CH:9][C:4]([CH2:3][CH2:2][NH:1][C:34]([C:35]4[CH:40]=[CH:39][N:38]=[CH:37][CH:36]=4)=[O:41])=[CH:5][CH:6]=3)=[CH:25][CH:24]=2)[CH2:30][CH2:31][CH2:32][CH2:33]1

Participants

5

Reactant 3

HCID 5922Isonicotinic AcidHCID 10868DicyclohexylcarbodiimideHCID 224627162-[4-(2-Aminoethyl)phenyl]-3-[4-[2-(1-pyrrolidinyl)ethoxy]benzyl]benzo[b]thiophene

Product 1

HCID 224627773-[4-[2-(1-Pyrrolidinyl)ethoxy]benzyl]-2-[4-[2-(4-pyridinylcarbonylamino)ethyl]phenyl]benzo[b]thiopheneYield 33%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-[4-(2-aminoethyl)phenyl]-3-[4-[2-(1-pyrrolidinyl)ethoxy]benzyl]benzo[b]thiophene (111 mg) in dichloromethane (3.0 mL) was treated isonicotinic acid (35 mg) and DCC (50 mg) sequentially and allowed to stir at ambient temperature for 25 h. The reaction mixture was then concentrated and fractionated by column chromatography with Et3N:MeOH:EtOAc (5:10:85) to afford the product (45 mg).

Workup

  1. concentrationThe reaction mixture was then concentrated

Sources & evidence

ORD record
ord-f54d6456eed04f3481cf8e620ec84e12
Source dataset
uspto-grants-2002_05
Patent number
US06391901B1

Reaction notes

Loading…