HCID 22479873, compound → HCID 178522019, compound

HRID 1353874Notes

Reaction equation

HRID 1353874 reaction equation
[O:1]=[C:2]([C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([C:21]4[N:25]=[CH:24][N:23](C(C5C=CC=CC=5)(C5C=CC=CC=5)C5C=CC=CC=5)[N:22]=4)[CH:19]=3)[N:14](C3CCCCO3)[N:13]=2)[CH:7]=1)=[O:4]>Cl.O1CCOCC1>[NH:23]1[CH:24]=[N:25][C:21]([C:18]2[CH:19]=[C:20]3[C:15](=[CH:16][CH:17]=2)[NH:14][N:13]=[C:12]3[C:8]2[CH:7]=[C:6]([NH:5][C:3](=[O:4])[C:2](=[O:1])[C:51]3[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=3)[CH:11]=[CH:10][CH:9]=2)=[N:22]1

Participants

4

Reactant 1

HCID 22479873HCID 22479873, compound

Product 1

HCID 178522019HCID 178522019, compoundYield 14%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

2-Oxo-N-(3-{1-perhydro-2H-pyran-2-yl-5[1-(triphenylmethyl)(1,2,4-triazol-3-yl)](1H-indazol-3-yl)}phenyl)-2-phenylacetamide was dissolved in 4 mL of 4.0 N HCl in 1,4-dioxane and the reaction was stirred at room temperature for 4 h. After neutralization with aqueous NaHCO3, the crude product was extracted in ethyl acetate and purified by preparative HPLC (0.014 g, 14% yield over 2 steps): 1H NMR (CD3OD) δ 8.80 (s, 1H), 8.39 (t, 1H), 8.21 (m, 2H), 8.13 (d, 1H), 7.94 (dt, 1H), 7.89 (dt, 1H), 7.82–7.69 (m, 3H), 7.64–7.57 (m, 3H); ES-MS (m/z) 409 [M+H]+.

Workup

  1. extractionAfter neutralization with aqueous NaHCO3, the crude product was extracted in ethyl acetate
  2. custompurified by preparative HPLC (0.014 g, 14% yield over 2 steps)

Sources & evidence

ORD record
ord-68265e552aab4a7da8c99bc209e85870
Source dataset
uspto-grants-2007_05
Patent number
US07220771B2

Reaction notes

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