Hydrochloric Acid → HCID 22479762, compound

HRID 1349674Notes

Reaction equation

HRID 1349674 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]#[N:18])[CH:15]=3)[N:10](C3CCCCO3)[N:9]=2)=[CH:4][CH:3]=1.[N:25]([Sn](CCCC)(CCCC)CCCC)=[N+:26]=[N-:27].O1CCOCC1.Cl>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]4[N:18]=[N:25][NH:26][N:27]=4)[CH:15]=3)[NH:10][N:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 4984872Tributyltin azideHCID 22480117HCID 22480117, compound

Product 1

HCID 22479762HCID 22479762, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The title compound was prepared from 3-(4-chlorophenyl)-1-perhydro-2H-pyran-2-yl-1H-indazole-5-carbonitrile (0.351 g, 1.04 mmol), azidotributyl tin (0.351 g, 0.627 mL, 2.29 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 6.0N aqueous solution of hydrogen chloride. Half of the solid obtained upon completion of the reaction was purified by preparatory HPLC (0.054 g, 0.18 mmol, 35% yield over 2 steps) 1H NMR (DMSO-d6) 13.7 (s, 1H), 8.8 (s, 1H), 8.1 (t, 3H), 7.8 (d, 1H), 7.6 (t, 2H); ES-MS (m/z) 297 [M+1]+.

Workup

  1. customHalf of the solid obtained upon completion of the reaction
  2. customwas purified by preparatory HPLC (0.054 g, 0.18 mmol, 35% yield over 2 steps) 1H NMR (DMSO-d6) 13.7 (s, 1H), 8.8 (s, 1H), 8.1 (t, 3H), 7.8 (d, 1H), 7.6 (t, 2H)

Sources & evidence

ORD record
ord-3eb0dfb5282341acae86fc4fa26c1d35
Source dataset
uspto-grants-2007_05
Patent number
US07211594B2

Reaction notes

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