5-(chloromethyl)-1,3-dimethyl-1H-1,2,4-triazole → Methyl 5-({6-cyclopentyl-4-hydroxy-6-[2-(4-methoxyphenyl)ethyl]-2-oxo-5,6-dihydro-2H-pyran-3-yl}methyl)isoxazol-3-ylcarbamate

HRID 1453194Notes

Reaction equation

HRID 1453194 reaction equation
Br[CH2:2][C:3]1[O:7][N:6]=[C:5]([NH:8][C:9](=[O:12])[O:10][CH3:11])[CH:4]=1.ClCC1N(C)N=C(C)N=1.[CH:22]1([C:27]2([CH2:35][CH2:36][C:37]3[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=3)[O:32][C:31](=[O:33])[CH2:30][C:29](=[O:34])[CH2:28]2)[CH2:26][CH2:25][CH2:24][CH2:23]1>>[CH:22]1([C:27]2([CH2:35][CH2:36][C:37]3[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=3)[O:32][C:31](=[O:33])[C:30]([CH2:2][C:3]3[O:7][N:6]=[C:5]([NH:8][C:9](=[O:12])[O:10][CH3:11])[CH:4]=3)=[C:29]([OH:34])[CH2:28]2)[CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

4

Reactant 3

HCID 131031005-(chloromethyl)-1,3-dimethyl-1H-1,2,4-triazoleHCID 13371029Methyl 5-(bromomethyl)isoxazol-3-ylcarbamateHCID 160761026-(4-methoxyphenethyl)-6-cyclopentyl-dihydro-3H-pyran-2,4-dione

Product 1

HCID 58762707Methyl 5-({6-cyclopentyl-4-hydroxy-6-[2-(4-methoxyphenyl)ethyl]-2-oxo-5,6-dihydro-2H-pyran-3-yl}methyl)isoxazol-3-ylcarbamateYield 13%

Procedure

The title compound was prepared as described in Example B(53), using methyl 5-(bromomethyl)isoxazol-3-ylcarbamate (prepared as described: Sircar, J. C.; Capiris, T. U.S. Pat. No. 4,489,077, Dec. 18, 1984) in place of 5-(chloromethyl)-1,3-dimethyl-1H-1,2,4-triazole, and using 6-cyclopentyl-6-[2-(4-methoxyphenyl)ethyl]dihydro-2H-pyran-2,4(3H)-dione in place of 6-[2-(3-chloro-4-methoxyphenyl)ethyl]-6-cyclopentyldihydro-2H-pyran-2,4(3H)-dione. Yield: 13%. 1H NMR (300 MHz, DMSO-d6) δ 1.15-1.65 (m, 8H), 1.80 (m, 2H), 2.25 (m, 1H), 2.39-2.51 (m, 3H, overlap with DMSO-d5), 2.68 (d, J=17.4 Hz, 1H), 3.51 (s, 2H), 3.56 (s, 3H), 3.61 (s, 3H), 6.24 (s, 1H), 6.72 (d, J=8.4 Hz, 2H), 6.95 (d, J=8.4 Hz, 2H), 10.47 (s, 1H), 11.15 (br s, 1H). LC-MS (APCI) calcd for C25H30N2O7: 470.21; found (M+H+) 471.1 m/z.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-6474bbd5098443318554fa53cb116076
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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