HCID 22480347, compound → HCID 178522014, compound

HRID 1272957Notes

Reaction equation

HRID 1272957 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]([C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][N:50]=3)=[O:48])[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]([C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][N:50]=3)=[O:48])[CH:43]=[CH:44][CH:45]=2)=[N:17]1

Participants

4

Reactant 1

HCID 22480347HCID 22480347, compound

Product 1

HCID 178522014HCID 178522014, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

[N-(3-{1-Perhydro-2H-pyran-2-yl-5-[1-(triphenylmethyl)(1,2,4-triazol-3-yl)](1H-indazol-3-yl)}phenyl)-2-pyridylcarboxamide 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 with ethyl acetate and purified by preparative HPLC. (0.037 g, 39% yield over 2 steps): 1H NMR (CD3OD) δ 8.81 (s, 1H), 8.76 (dt, 1H), 8.55 (t, 1H), 8.45 (br s, 1H), 8.25 (dt, 1H), 8.12 (dd, 1H), 8.09 (td, 1H), 8.00 (dt, 1H), 7.85 (dt, 2H), 7.73 (d, 1H), 7.65 (ddd, 1H), 7.59 (t, 1H); ES-MS (m/z) 382 [M+H]+.

Workup

  1. extractionAfter neutralization with aqueous NaHCO3, the crude product was extracted with ethyl acetate
  2. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-1cbf1717ae0f4931833fdfaeec6bce96
Source dataset
uspto-grants-2007_04
Patent number
US07208513B2

Reaction notes

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