2-(Dimethylamino)-N-(3-{1-perhydro-2H-pyran-2-yl-5-[1-(triphenylmethyl)(1,2,4-triazol-3-yl)](1H-indazol-3-yl)) phenyl)acetamide → N-[3-(5-(1H-1,2,4-Triazol-3-Yl)(1H-Indazol-3-Yl))Phenyl]-2-(Dimethylamino)Acetamide

HRID 1353853Notes

Reaction equation

HRID 1353853 reaction equation
[CH3:1][N:2]([CH3:52])[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]>Cl.O1CCOCC1>[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][N:2]([CH3:1])[CH3:52])[CH:12]=[CH:11][CH:10]=2)=[N:23]1

Participants

4

Reactant 1

HCID 224800272-(Dimethylamino)-N-(3-{1-perhydro-2H-pyran-2-yl-5-[1-(triphenylmethyl)(1,2,4-triazol-3-yl)](1H-indazol-3-yl)) phenyl)acetamide

Product 1

HCID 178483932N-[3-(5-(1H-1,2,4-Triazol-3-Yl)(1H-Indazol-3-Yl))Phenyl]-2-(Dimethylamino)AcetamideYield 13%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

2-(Dimethylamino)-N-(3-{1-perhydro-2H-pyran-2-yl-5-[1-(triphenylmethyl)(1,2,4-triazol-3-yl)](1H-indazol-3-yl)}phenyl)acetamide was dissolved in 4 mL of 4.0 N HCl in 1,4-dioxane and the reaction was stirred at room temperature for 3 hours. After neutralization with aqueous NaHCO3, the reaction mixture was evaporated to dryness and purified by preparatory HPLC. (0.023 g, 13% yield over 2 steps): 1H NMR (CD3OD) δ 8.7 (d, 1H), 8.32 (br s, 1H), 8.17 (t, 1H), 8.05 (dd, 1H), 7.7 (t, 2H), 7.6 (dd, 1H), 7.4 (t, 1H), 3.18 (s, 2H), 2.38 (s, 6H); ES-MS (m/z) 362 [M+H]+.

Workup

  1. customAfter neutralization with aqueous NaHCO3, the reaction mixture was evaporated to dryness
  2. custompurified by preparatory HPLC

Sources & evidence

ORD record
ord-00c041acfdeb4234b04b9020bc4aad97
Source dataset
uspto-grants-2007_05
Patent number
US07220771B2

Reaction notes

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