2-Methoxy-N-(3-{1-perhydro-2H-pyran-2-yl-5[-1-(triphenylmethyl)(1,2,4-triazol-3yl)]-(1H-indazol-3-yl)}phenyl)acetamide → HCID 178496385, compound

HRID 1272841Notes

Reaction equation

HRID 1272841 reaction equation
[CH3:1][O:2][CH2:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([C:22]4[N:26]=[CH:25][N:24](C(C5C=CC=CC=5)(C5C=CC=CC=5)C5C=CC=CC=5)[N:23]=4)[CH:20]=3)[N:15](C3CCCCO3)[N:14]=2)[CH:8]=1)=[O:5]>O1CCOCC1.Cl>[NH:24]1[CH:25]=[N:26][C:22]([C:19]2[CH:20]=[C:21]3[C:16](=[CH:17][CH:18]=2)[NH:15][N:14]=[C:13]3[C:9]2[CH:8]=[C:7]([NH:6][C:4](=[O:5])[CH2:3][O:2][CH3:1])[CH:12]=[CH:11][CH:10]=2)=[N:23]1

Participants

4

Reactant 1

HCID 224800982-Methoxy-N-(3-{1-perhydro-2H-pyran-2-yl-5[-1-(triphenylmethyl)(1,2,4-triazol-3yl)]-(1H-indazol-3-yl)}phenyl)acetamide

Product 1

HCID 178496385HCID 178496385, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

Hydrolysis was performed by stirring 2-methoxy-N-(3-{1-perhydro-2H-pyran-2-yl-5-[1-(triphenylmethyl)(1,2,4-triazol-3-yl)](1H-indazol-3-yl)}phenyl)acetamide (0.141 g, 0.207 mmol) in 4 mL of 4.0 N commercial solution of HCl in dioxane and 2 mL of 6.0N aqueous HCl, at room temperature for 18 hours. The title compound was purified by preparative HPLC (15–80% acetonitrile in water) (0.033 g, 46% yield) 1H NMR (DMSO-d6) δ 13.5 (br s, 1H), 10.0 (s, 1H), 8.7 (s, 1H), 8.4 (br s, 1H), 8.3 (s, 1H), 8.1 (d, 1H), 7.8 (d, 1H), 7.7 (d, 2H), 7.5 (dd, 1H), 4.06 (s, 2H), 3.4 (s, 3H); ES-MS (m/z) 349 [M+1]+.

Workup

  1. customHydrolysis
  2. customThe title compound was purified by preparative HPLC (15–80% acetonitrile in water) (0.033 g, 46% yield) 1H NMR (DMSO-d6) δ 13.5 (br s, 1H), 10.0 (s, 1H), 8.7 (s, 1H), 8.4 (br s, 1H), 8.3 (s, 1H), 8.1 (d, 1H), 7.8 (d, 1H), 7.7 (d, 2H), 7.5 (dd, 1H), 4.06 (s, 2H), 3.4 (s, 3H)

Sources & evidence

ORD record
ord-1d8334b736a34cbd903314e1699360b7
Source dataset
uspto-grants-2007_04
Patent number
US07208513B2

Reaction notes

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