4-Methyl-5-(2-hydroxyethyl)thiazole → 3-Fluoro-N-{4-[2-(4-methyl-1,3-thiazol-5-yl)ethoxy]-1-naphthyl}-5-piperidin-1-ylbenzamide

HRID 1641228Notes

Reaction equation

HRID 1641228 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.[CH3:36][C:37]1[N:38]=[CH:39][S:40][C:41]=1[CH2:42][CH2:43]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][CH2:42][C:41]2[S:40][CH:39]=[N:38][C:37]=2[CH3:36])=[CH:10][CH:9]=1)=[O:19]

Participants

4

Reactant 3

HCID 11364-Methyl-5-(2-hydroxyethyl)thiazoleHCID 10923237tert-Butyl (4-hydroxynaphthalen-1-yl)carbamateHCID 595531803-Fluoro-5-piperidinylbenzoic acid

Product 1

HCID 595534763-Fluoro-N-{4-[2-(4-methyl-1,3-thiazol-5-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 2-(4-methylthiazol-5-yl)-ethanol according to conditions described in general procedure D. A pink solid is produced (12 mg). Mp: 221-222° C.; 1H NMR (300 MHz, CDCl3) δ 1.62-1.69(m, 6H), 2.50(s, 3H), 3.20-3.27(m, 5H), 3.40(t, J=6.3 Hz, 1H), 4.34(t, J=6.0 Hz, 1H), 4.46(t, J=6.6 Hz, 1H), 6.73-6.82(m, 2H), 6.98(d, J=8.1 Hz, 1H), 7.06-7.10(m, 1H), 7.31-7.35(m, 1H), 7.50-7.59(m, 2H), 7.73(d, J=9.3 Hz, 1H), 7.83(d, J=7.8 Hz, 1H), 7.93(s, 1H), 8.32-8.35(m, 1H), 8.60-8.62(m, 1H); MS 490 (M+1).

Workup

  1. customA pink solid is produced (12 mg)

Sources & evidence

ORD record
ord-fc531691b1f1418cad20808736d917e0
Source dataset
uspto-grants-2012_02
Patent number
US08114873B2

Reaction notes

Loading…