HCID 22480185, compound → HCID 178520431, compound

HRID 2183297Notes

Reaction equation

HRID 2183297 reaction equation
O1CCCCC1[N:7]1[C:15]2[C:10](=[CH:11][C:12]([C:16]3[N:20]=[CH:19][N:18](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:17]=3)=[CH:13][CH:14]=2)[C:9]([C:40]2[CH:41]=[C:42]([NH:46][C:47](=[O:56])/[CH:48]=[CH:49]/[C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)[CH:43]=[CH:44][CH:45]=2)=[N:8]1>Cl.O1CCOCC1>[NH:18]1[CH:19]=[N:20][C:16]([C:12]2[CH:11]=[C:10]3[C:15](=[CH:14][CH:13]=2)[NH:7][N:8]=[C:9]3[C:40]2[CH:41]=[C:42]([NH:46][C:47](=[O:56])/[CH:48]=[CH:49]/[C:50]3[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=3)[CH:43]=[CH:44][CH:45]=2)=[N:17]1

Participants

4

Reactant 1

HCID 22480185HCID 22480185, compound

Product 1

HCID 178520431HCID 178520431, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

(2E)-N-(3-{1-Perhydro-2H-pyran-2-yl-5-[1-(triphenylmethyl)(1,2,4-triazol-3-yl)](1H-indazol-3-yl)}phenyl)-3-phenylprop-2-enamide 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 compound precipitated out of solution. The solid was collected by filtration and was purified by preparative HPLC. (0.036 g, 33% yield over 2 steps): 1H NMR (CD3OD) δ 8.7 (s, 1H), 8.3 (br s, 1H), 8.1 (br d, 1H), 7.8-7.6 (m, 6H), 7.54 (t, 1H), 7.45-7.4 (m, 3H), 6.85 (d, 1H); ES-MS (m/z) 407 [M+H]+.

Workup

  1. customAfter neutralization with aqueous NaHCO3, the compound precipitated out of solution
  2. filtrationThe solid was collected by filtration
  3. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-4c95c4ab7aba4b07851f3aba6821abd8
Source dataset
uspto-grants-2005_05
Patent number
US06897231B2

Reaction notes

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