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 1272968Notes

Reaction equation

HRID 1272968 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-d30c46f315bf4014a18a4cbb3488ff4e
Source dataset
uspto-grants-2007_04
Patent number
US07208513B2

Reaction notes

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