HCID 89740577, compound → HCID 71695775, compound

HRID 925407Notes

Reaction equation

HRID 925407 reaction equation
[N:1]1[NH:2][N:3]=[N:4][C:5]=1[CH2:6][NH:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13]([O:17]CC1C=CC=CC=1)[N:12]=[CH:11]2>CO.[Pd]>[N:4]1[NH:3][N:2]=[N:1][C:5]=1[CH2:6][NH:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13]([OH:17])[N:12]=[CH:11]2

Participants

4

Reactant 1

HCID 89740577HCID 89740577, compound

Product 1

HCID 71695775HCID 71695775, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-((2H-tetrazol-5-yl)methyl)-1-(benzyloxy)-1H-indazol-5-amine (43 mg, 0.14 mmol) in dry MeOH (10 mL) was added 10% Pd on charcoal (5 mg). The reaction was stirred under hydrogen atmosphere overnight, and then the solution was filtered over filter paper. Solvent was removed using a rotatory evaporator to provide the desired product, 76, (32 mg, 0.14 mmol) as a pale green solid in quantitative yield. 1H NMR (500 MHz, DMSO) δ 7.95 (s, 1H), 7.72 (s, 1H), 7.60 (d, J=8.5 Hz, 1H), 7.02 (dd, J=1.5, 8.5 Hz, H), 5.35 (s, 2H). 13C NMR (125 MHz, DMSO) δ 155.90, 140.24, 134.21, 129.74, 127.39, 123.31, 120.85, 110.81, 60.94. MS (ESI, CH3OH): [C9H9N7O] m/z 232.1 ([M+H]+).

Workup

  1. filtrationthe solution was filtered
  2. filtrationover filter paper
  3. customSolvent was removed
  4. customa rotatory evaporator

Sources & evidence

ORD record
ord-cd076d5faedd449d89f3e5b2310a0af9
Source dataset
uspto-grants-2016_03
Patent number
US09284299B2

Reaction notes

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