Hydrochloric Acid → 5-{3-[4-(Methylethyl)Phenyl]-1H-Indazol-5-Yl}-2H-1,2,3,4-Tetrazole

HRID 2183168Notes

Reaction equation

HRID 2183168 reaction equation
[CH3:1][CH:2]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:19]#[N:20])[CH:17]=3)[N:12](C3CCCCO3)[N:11]=2)=[CH:6][CH:5]=1)[CH3:3].[N:27]([Sn](CCCC)(CCCC)CCCC)=[N+:28]=[N-:29].O1CCOCC1.Cl>C1(C)C=CC=CC=1.[OH-].[Na+]>[CH3:1][CH:2]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:19]4[N:20]=[N:27][NH:28][N:29]=4)[CH:17]=3)[NH:12][N:11]=2)=[CH:8][CH:9]=1)[CH3:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 4984872Tributyltin azideHCID 224802413-[4-(methylethyl)phenyl]-1-perhydro-2H-pyran-2-yl-1H-indazole-5-carbonitrile

Product 1

HCID 224801015-{3-[4-(Methylethyl)Phenyl]-1H-Indazol-5-Yl}-2H-1,2,3,4-TetrazoleYield 80%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 14798Sodium HydroxideSolvent

Procedure

The title compound was prepared from 3-[4-(methylethyl)phenyl]-1-perhydro-2H-pyran-2-yl-1H-indazole-5-carbonitrile (0.095 g, 0.307 mmol), azidotributyl tin (0.744 g, 0.689 mL, 2.33 mmol) in toluene (10 mL) as described for the preparation of compound 167. Deprotection was effected by treating a dioxane solution (5 mL) with 5 mL of 6.0 N aqueous solution of hydrogen chloride. The solid obtained upon completion of the reaction was partially dissolved in 2.0 N aqueous sodium hydroxide and was extracted in ethyl acetate (4×15 mL). (0.260 g, 0.85 mmol, 80% yield over 2 steps): 1H NMR (DMSO-d6) δ 13.5 (br s, 1H), 8.7 (s, 1H), 8.1 (d, 1H), 7.9 (d, 2H), 7.8 (d, 1H), 7.4 (d, 2H), 3.0 (septet, 1H), 1.3 (d, 6H); ES-MS (m/z) 305 [M+1]+.

Workup

  1. customThe solid obtained upon completion of the reaction
  2. extractionwas extracted in ethyl acetate (4×15 mL)

Sources & evidence

ORD record
ord-3b539cf0c6e14260ad0aff8c0ae99c74
Source dataset
uspto-grants-2005_05
Patent number
US06897231B2

Reaction notes

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