Pentylamine → HCID 17838262, compound

HRID 1352172Notes

Reaction equation

HRID 1352172 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([NH:10][CH:11]3[CH2:16][CH2:15][C:14](=O)[CH2:13][CH2:12]3)=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[CH2:18]([NH2:23])[CH2:19][CH2:20][CH2:21][CH3:22].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl.CO>CO>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([NH:10][CH:11]3[CH2:16][CH2:15][CH:14]([NH:23][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:13][CH2:12]3)=[CH:7][CH:8]=2)[CH:3]=[N:2]1

Participants

6

Reactant 4

HCID 8060PentylamineHCID 5049666Sodium triacetoxyborohydrideHCID 178382714-(1H-5-Indazolylamino)-1-cyclohexanone2×HCID 21893726Hydrochloride methanol

Product 1

HCID 17838262HCID 17838262, compoundYield 13.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-(1H-5-Indazolylamino)-1-cyclohexanone (intermediate 3) (57 mg) and amylamine (44 mg) were dissolved in methanol (1 ml), and sodium triacetoxyborohydride (105 mg) was added by portions to the solution at room temperature. The reaction mixture was stirred at room temperature for 18 hr. Hydrochloric acid-methanol was then added thereto, and the reaction mixture was stirred and was then concentrated. The residue was purified by HPLC [0.5% aqueous trifluoroacetic acid solution/acetonitrile] to give an anti-form compound (10 mg) and a syn-form compound (10 mg).

Workup

  1. stirringthe reaction mixture was stirred
  2. concentrationwas then concentrated
  3. customThe residue was purified by HPLC [0.5% aqueous trifluoroacetic acid solution/acetonitrile]

Sources & evidence

ORD record
ord-f76352db80254a8aa209109521c494cc
Source dataset
uspto-grants-2007_05
Patent number
US07217722B2

Reaction notes

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