1-(2-Hydroxyethyl)-2-pyrrolidinone → 3-Fluoro-5-piperidin-1-yl-N-[4-(pyridin-4-ylmethoxy)-1-naphthyl]benzamide

HRID 1641229Notes

Reaction equation

HRID 1641229 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>>[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][CH2:43][C:42]2[CH:37]=[CH:38][N:39]=[CH:40][CH:41]=2)=[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 595532863-Fluoro-5-piperidin-1-yl-N-[4-(pyridin-4-ylmethoxy)-1-naphthyl]benzamide

Procedure

Compound is prepared from tert-butyl(4-hydroxy-1-naphthyl)carbamate, 3-fluoro-5-piperidin-1-yl-benzoic acid and 1-(2-hydroxy-ethyl)-pyrrolidin-2-one according to conditions described in general procedure D. A pink solid is produced (38 mg). Mp: 69-71° C.; 1H NMR (300 MHz, DMSO-d6) δ 1.58(s, 6H), 3.28(s, 4H), 5.42(s, 2H), 6.95(d, J=8.4 Hz, 1H), 7.06(d, J =8.1 Hz, 1H), 7.15(d, J=6.9 Hz, 1H), 7.44(s, 1H), 7.55-7.60(m, 4H), 7.85-7.92(m, 1H), 8.30-8.38(m, 1H), 8.60-8.63(m, 1H), 10.26(s, 1H); MS 456 (M+1).

Workup

  1. customA pink solid is produced (38 mg)

Sources & evidence

ORD record
ord-e47ffc9ad3404ee58b44cadc4cb7c3ac
Source dataset
uspto-grants-2012_02
Patent number
US08114873B2

Reaction notes

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