Hydrochloric Acid → HCID 22479797, compound

HRID 1353736Notes

Reaction equation

HRID 1353736 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, 0.3 10 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-d3c70a87b80b4ada99f3e0020e683ee2
Source dataset
uspto-grants-2007_05
Patent number
US07220771B2

Reaction notes

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