Hydrochloric Acid → HCID 22480144, compound

HRID 1349666Notes

Reaction equation

HRID 1349666 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15]#[N:16])[CH:13]=2)[N:8](C2CCCCO2)[N:7]=1.[N:23]([Sn](CCCC)(CCCC)CCCC)=[N+:24]=[N-:25].Cl>C1(C)C=CC=CC=1.O1CCOCC1>[N:23]1[NH:24][N:25]=[N:16][C:15]=1[C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[NH:8][N:7]=[C:6]2[C:2]1[O:1][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4984872Tributyltin azideHCID 22479916HCID 22479916, compound

Product 1

HCID 22480144HCID 22480144, compoundYield 4.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent2×

Procedure

The title compound was prepared from 3-(2-furyl)-1-perhydro-2H-pyran-2-yl-1H-indazole-5-carbonitrile (0.095 g, 0.307 mmol), azidotributyl tin (0.245 g, 0.202 mL, 0.74 mmol) in toluene (8 mL) as described for the preparation of compound 167. Deprotection was effected by treating a dioxane solution (5 mL) with 8 mL of 4.0N solution of hydrogen chloride in 1,4-dioxane. The compound was purified by preparative HPLC (10–100% acetonitrile in H2O, 20 min) (0.008 g, 0.032 mmol, 4.7% yield over 2 steps): 1H NMR (DMSO-d6) δ 13.6 (br s, 1H), 8.8 (s, 1H), 8.1 (d, 1H), 7.9 (d, 1H), 7.8 (d, 1H), 7.1 (d, 1H), 6.7 (dd, 1H); ES-MS (m/z) 253 [M+1]+.

Workup

  1. customThe compound was purified by preparative HPLC (10–100% acetonitrile in H2O, 20 min) (0.008 g, 0.032 mmol, 4.7% yield over 2 steps)

Sources & evidence

ORD record
ord-01118c82248248cf8628361d4651edb3
Source dataset
uspto-grants-2007_05
Patent number
US07211594B2

Reaction notes

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