HCID 22480296, compound → HCID 178522021, compound

HRID 1353864Notes

Reaction equation

HRID 1353864 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10](=[O:59])[C:11]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]3[C:28]4[C:23](=[CH:24][CH:25]=[C:26]([C:29]5[N:33]=[CH:32][N:31](C(C6C=CC=CC=6)(C6C=CC=CC=6)C6C=CC=CC=6)[N:30]=5)[CH:27]=4)[N:22](C4CCCCO4)[N:21]=3)[CH:15]=2)=[O:12])=[CH:2]1>Cl.O1CCOCC1>[NH:31]1[CH:32]=[N:33][C:29]([C:26]2[CH:27]=[C:28]3[C:23](=[CH:24][CH:25]=2)[NH:22][N:21]=[C:20]3[C:16]2[CH:15]=[C:14]([NH:13][C:11](=[O:12])[C:10]([C:3]3[C:4]4[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=4)[NH:1][CH:2]=3)=[O:59])[CH:19]=[CH:18][CH:17]=2)=[N:30]1

Participants

4

Reactant 1

HCID 22480296HCID 22480296, compound

Product 1

HCID 178522021HCID 178522021, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

2-Indol-3-yl-2-oxo-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 reaction mixture was evaporated to dryness and purified by preparative HPLC. (0.018 g, 16% yield over 2 steps): 1H NMR (CD3OD) δ 11.93 (s, 1H), 10.53 (s, 1H), 8.95 (s, 1H), 8.86 (s, 1H), 8.55 (s, 1H), 8.52 (s, 1H), 8.41 (dd, 1H), 8.14 (dd, 1H), 8.0 (d, 1H), 7.89 (d, 1H), 7.75 (d, 1H), 7.64–7.54 (m, 2H), 7.34–7.30 (m, 2H); ES-MS (m/z) 449.

Workup

  1. customAfter neutralization with aqueous NaHCO3, the reaction mixture was evaporated to dryness
  2. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-f08107fbbab44252b08a2e91c074dac0
Source dataset
uspto-grants-2007_05
Patent number
US07220771B2

Reaction notes

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