1-(3-Hydroxypropyl)pyrrolidin-2-one → 3-Fluoro-N-{4-[3-(2-oxopyrrolidin-1-yl)propoxy]-1-naphthyl}-5-piperidin-1-ylbenzamide

HRID 1641230Notes

Reaction equation

HRID 1641230 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][CH2:39][N:40]1[CH2:44][CH2:43][CH2:42][C:41]1=[O:45]>>[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][CH2:39][N:40]2[CH2:44][CH2:43][CH2:42][C:41]2=[O:45])=[CH:10][CH:9]=1)=[O:19]

Participants

4

Reactant 3

HCID 5667441-(3-Hydroxypropyl)pyrrolidin-2-oneHCID 10923237tert-Butyl (4-hydroxynaphthalen-1-yl)carbamateHCID 595531803-Fluoro-5-piperidinylbenzoic acid

Product 1

HCID 595531013-Fluoro-N-{4-[3-(2-oxopyrrolidin-1-yl)propoxy]-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-(3-hydroxy-propyl)-pyrrolidin-2-one according to conditions described in general procedure D. A pink solid is produced (42 mg). Mp: 88-89° C.; 1H NMR (300 MHz, CDCl3) δ 1.69(s, 6H), 1.95-2.04(m, 2H), 2.10-2.18(m, 2H), 2.34-2.39(m, 2H), 3.26(s, 4H), 3.37-3.45(m, 2H), 3.50-3.55(m, 2H), 4.09-4.13(m, 2H), 6.72-6.77(m, 2H), 7.03(d, J=8.4 Hz, 1H), 7.33(s, 1H), 7.46-7.55(m, 2H), 7.63(d, J=7.8 Hz, 1H), 7.82(d, J=7.5 Hz, 1H), 8.23(s, 1H), 8.27-8.30 (m, 1H); MS 490 (M+1).

Workup

  1. customA pink solid is produced (42 mg)

Sources & evidence

ORD record
ord-f07c12ac706c498486b5b3304fcd8282
Source dataset
uspto-grants-2012_02
Patent number
US08114873B2

Reaction notes

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