Acetic Acid → HCID 22567151, compound

HRID 1678222Notes

Reaction equation

HRID 1678222 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[C:7]2[NH2:13])([O-:3])=[O:2].[CH:14](=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>C(Cl)Cl>[CH2:14]([NH:13][C:7]1[C:6]2[C:10](=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[NH:9][N:8]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 14798Sodium HydroxideHCID 31366553-Amino-5-nitroindazoleHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 22567151HCID 22567151, compoundYield 32.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 5-nitro-1H-indazol-3-ylamine (0.025 g, 0.140 mmol) and benzaldehyde (0.067 g, 0.60 mmol) in CH2Cl2 (3.0 mL) was added acetic acid (0.024 mL, 0.42 mmol) followed by sodium triacetoxyborohydride (0.059 g, 0.28 mmol). The resulting solution was allowed to stir at room temperature for about 19 hours. The reaction solution was diluted with CH2Cl2 (5 mL) and treated with an aqueous solution of NaOH (1N, 5 mL). The two phases were separated and the organic solvent was removed under reduced pressure. The residue was further purified by preparative HPLC (Thermo Hypersil-Keystone 250×21.2 mm 8 Hypersil® HS C18 column; 5% acetonitrile/0.1 M aqueous ammonium acetate-100% acetonitrile over 20 min, 100% acetonitrile hold 5 minutes, 21 mL/min) to give benzyl-(5-nitro-1H-indazol-3-yl)-amine (0.012 g, 0.046 mmol) as an orange solid. RP-HPLC (Table 1, Method e) Rt 2.15 min.; m/z: (M+H)+ 269.

Workup

  1. customThe two phases were separated
  2. customthe organic solvent was removed under reduced pressure
  3. customThe residue was further purified by preparative HPLC (Thermo Hypersil-Keystone 250×21.2 mm 8 Hypersil® HS C18 column; 5% acetonitrile/0.1 M aqueous ammonium acetate-100% acetonitrile over 20 min, 100% acetonitrile hold 5 minutes, 21 mL/min)

Sources & evidence

ORD record
ord-d823513eb5824641a184ee626ee52b68
Source dataset
uspto-grants-2011_08
Patent number
US08008481B2

Reaction notes

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