HCID 22480185, compound → HCID 178520431, compound

HRID 1272943Notes

Reaction equation

HRID 1272943 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-7050f82c21dc438f8893a57ed936803d
Source dataset
uspto-grants-2007_04
Patent number
US07208513B2

Reaction notes

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