2-Cyclohexyl-N-(3-{1-perhydro-2H-pyran-2-yl-5-[1-(triphenylmethyl)(1,2,4-triazol-3-yl)](1H-indazol-3-yl)}phenyl)acetamide → N-[3-(5-(1H-1,2,4-Triazol-3-YL)(1H-indazol-3-YL))phenyl]-2-cyclohexylacetamide

HRID 1353876Notes

Reaction equation

HRID 1353876 reaction equation
[CH:1]1([CH2:7][C:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]3[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([C:26]5[N:30]=[CH:29][N:28](C(C6C=CC=CC=6)(C6C=CC=CC=6)C6C=CC=CC=6)[N:27]=5)[CH:24]=4)[N:19](C4CCCCO4)[N:18]=3)[CH:12]=2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>Cl.O1CCOCC1>[NH:28]1[CH:29]=[N:30][C:26]([C:23]2[CH:24]=[C:25]3[C:20](=[CH:21][CH:22]=2)[NH:19][N:18]=[C:17]3[C:13]2[CH:12]=[C:11]([NH:10][C:8](=[O:9])[CH2:7][CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)[CH:16]=[CH:15][CH:14]=2)=[N:27]1

Participants

4

Reactant 1

HCID 224801082-Cyclohexyl-N-(3-{1-perhydro-2H-pyran-2-yl-5-[1-(triphenylmethyl)(1,2,4-triazol-3-yl)](1H-indazol-3-yl)}phenyl)acetamide

Product 1

HCID 178520226N-[3-(5-(1H-1,2,4-Triazol-3-YL)(1H-indazol-3-YL))phenyl]-2-cyclohexylacetamideYield 34%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

2-Cyclohexyl-N-(3-{1-perhydro-2H-pyran-2-yl-5-[1-(triphenylmethyl)(1,2,4-triazol-3-yl)](1H-indazol-3-yl)}phenyl)acetamide was dissolved in 4 mL of 4.0 N HCl in 1,4-dioxane and the reaction was stirred at room temperature overnight. After neutralization with aqueous NaHCO3, the crude product was extracted in ethyl acetate and purified by preparative HPLC (0.034 g, 34% yield over 2 steps): 1H NMR (CD3OD) δ 8.75 (s, 1H), 8.38 (br s, 2H), 8.20 (s, 1H), 8.10 (d, 1H), 7.76 (td, 2H), 7.70 (d, 1H), 7.51 (t, 1H), 2.30 (d, 2H), 1.90 (m, 1H), 1.78 (m, 4H), 1.3 (m, 4H), 1.07 (m, 2H); ES-MS (m/z) 401 [M+H]+.

Workup

  1. extractionAfter neutralization with aqueous NaHCO3, the crude product was extracted in ethyl acetate
  2. custompurified by preparative HPLC (0.034 g, 34% yield over 2 steps)

Sources & evidence

ORD record
ord-c5eada50b8dc46ee97177214a65ee056
Source dataset
uspto-grants-2007_05
Patent number
US07220771B2

Reaction notes

Loading…