Hydrochloric Acid → HCID 22479797, compound

HRID 1349670Notes

Reaction equation

HRID 1349670 reaction equation
O1CCCCC1[N:7]1[C:15]2[C:10](=[CH:11][C:12]([C:16]#[N:17])=[CH:13][CH:14]=2)[C:9]([C:18]2[CH:22]=[CH:21][S:20][CH:19]=2)=[N:8]1.[N:23]([Sn](CCCC)(CCCC)CCCC)=[N+:24]=[N-:25].O1CCOCC1.Cl>C1(C)C=CC=CC=1.O1CCCC1>[N:23]1[NH:24][N:25]=[N:17][C:16]=1[C:12]1[CH:11]=[C:10]2[C:15](=[CH:14][CH:13]=1)[NH:7][N:8]=[C:9]2[C:18]1[CH:22]=[CH:21][S:20][CH:19]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 4984872Tributyltin azideHCID 22480181HCID 22480181, compound

Product 1

HCID 22479797HCID 22479797, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared from 1-perhydro-2H-pyran-2-yl-3-(3-thienyl)-1H-indazole-5-carbonitrile (0.233 g, 0.75 mmol), azidotributyl tin (0.375 g, 0.310 mL, 1.13 mmol) in toluene (10 mL) as described for the preparation of Example 167. Deprotection was effected by treating a dioxane solution (5 mL) with 5 mL of 6.0N aqueous solution of hydrogen chloride. The solid obtained upon completion of the reaction was partially dissolved in 3 mL of tetrahydrofuran and was precipitated out by adding 20 mL of hexanes (0.108 g, 0.85 mmol, 79% yield over 2 steps): 1H NMR (DMSO-d6) δ 13.5 (br s, 1H), 8.8 (s, 1H), 8.2 (t, 1H), 8.1 (dd, 1H), 7.8–7.7 (m, 3H); ES-MS (m/z) 269 [M+1]+.

Workup

  1. customas described for the preparation of Example 167
  2. customThe solid obtained upon completion of the reaction
  3. customwas precipitated out

Sources & evidence

ORD record
ord-78a9f6250ab7413493d443665aa5e1a7
Source dataset
uspto-grants-2007_05
Patent number
US07211594B2

Reaction notes

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