1-(2-Hydroxyethyl)-2-pyrrolidinone → 3-Fluoro-N-{4-[2-(2-oxopyrrolidin-1-yl)ethoxy]-1-naphthyl}-5-piperidin-1-ylbenzamide

HRID 1641232Notes

Reaction equation

HRID 1641232 reaction equation
C(O[C:6](=[O:19])[NH:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([OH:18])=[CH:10][CH:9]=1)(C)(C)C.[F:20][C:21]1[CH:22]=[C:23]([CH:27]=[C:28]([N:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)[CH:29]=1)C(O)=O.O[CH2:37][CH2:38][N:39]1[CH2:43][CH2:42][CH2:41][C:40]1=[O:44]>>[F:20][C:21]1[CH:22]=[C:23]([CH:27]=[C:28]([N:30]2[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]2)[CH:29]=1)[C:6]([NH:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([O:18][CH2:37][CH2:38][N:39]2[CH2:43][CH2:42][CH2:41][C:40]2=[O:44])=[CH:10][CH:9]=1)=[O:19]

Participants

4

Reactant 3

HCID 769801-(2-Hydroxyethyl)-2-pyrrolidinoneHCID 10923237tert-Butyl (4-hydroxynaphthalen-1-yl)carbamateHCID 595531803-Fluoro-5-piperidinylbenzoic acid

Product 1

HCID 595533033-Fluoro-N-{4-[2-(2-oxopyrrolidin-1-yl)ethoxy]-1-naphthyl}-5-piperidin-1-ylbenzamide

Procedure

Compound is prepared from tert-butyl(4-hydroxy-1-naphthyl)carbamate, 3-fluoro-5-piperidin-1-yl-benzoic acid and 1-(2-hydroxyethyl)-pyrrolidin-2-one according to conditions described in general procedure D. A white solid is produced (27 mg). Mp: 161-162° C.; 1H NMR (300 MHz, CDCl3) δ 1.62-1.70(m, 6H), 1.99-2.09(m, 2H), 2.35-2.44(m, 2H), 3.16-3.27(m, 2H), 3.63-3.68(m, 2H), 3.84(d, J=5.1 Hz, 2H), 4.26(d, J=4.8 Hz, 2H), 6.73-6.79(m, 2H), 6.70(d, J=8.4 Hz, 1H), 7.32(s, 1H), 7.49-7.58(m, 2H), 7.68(d, J=8.1 Hz, 1H), 7.84(d, J=7.8 Hz, 1H), 8.03(s, 1H), 8.24-8.27(m, 1H); MS 476 (M+1).

Workup

  1. customA white solid is produced (27 mg)

Sources & evidence

ORD record
ord-76a036db1a7b488c9b2a981595c4e220
Source dataset
uspto-grants-2012_02
Patent number
US08114873B2

Reaction notes

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