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

HRID 1453208Notes

Reaction equation

HRID 1453208 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]([CH:43]([F:45])[F:44])=[C:39]([F:46])[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]([CH:43]([F:45])[F:44])=[C:39]([F:46])[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 587624916-cyclopentyl-6-{2-[4-(difluoromethyl)-3-fluorophenyl]ethyl}-dihydro-2H-pyran-2,4(3H)-dione

Product 1

HCID 58762241Methyl 5-[(6-cyclopentyl-6-{2-[4-(difluoromethyl)-3-fluorophenyl]ethyl}-4-hydroxy-2-oxo-5,6-dihydro-2H-pyran-3-yl)methyl]isoxazol-3-ylcarbamateYield 6%

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-(difluoromethyl)-3-fluorophenyl]ethyl}-dihydro-2H-pyran-2,4(3H)-dione (Example B(69), Step 3) in place of 6-[2-(3-chloro-4-methoxyphenyl)ethyl]-6-cyclopentyldihydro-2H-pyran-2,4(3H)-dione. Yield: 6%. 1H NMR (300 MHz, DMSO-d6) δ 1.18-1.75 (m, 8H), 1.94 (m, 2H), 2.35 (m, 1H), 2.40-2.70 (m, 3H, overlap with DMSO-d5), 2.76 (d, J=18.3 Hz, 1H), 3.59 (m, 2H, overlap with H2O), 3.63 (s, 3H), 6.31 (s, 1H), 7.08 (t, J=55 Hz, overlap with m, combined: 3H), 7.50 (t, J=7.5 Hz, 1H), 10.55 (s, 1H), 11.26 (s, 1H). LC-MS (APCI) calcd for C25H27F3N2O6: 508.18; found (M+H+): 509.1 m/z.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-dac76e98e2a24c918fcb9b42bee74813
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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