Isobutylamine → N1-(1H-5-Indazolyl)-N4-isobutyl-1,4-cyclohexanediamine

HRID 1352170

Reaction equation

HRID 1352170 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]([NH2:22])[CH:19]([CH3:21])[CH3:20].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:22][CH2:18][CH:19]([CH3:21])[CH3:20])[CH2:13][CH2:12]3)=[CH:7][CH:8]=2)[CH:3]=[N:2]1

Participants

6

Reactant 4

HCID 6558IsobutylamineHCID 5049666Sodium triacetoxyborohydrideHCID 178382714-(1H-5-Indazolylamino)-1-cyclohexanone2×HCID 21893726Hydrochloride methanol

Product 1

HCID 17838119N1-(1H-5-Indazolyl)-N4-isobutyl-1,4-cyclohexanediamineYield 11.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-(1H-5-Indazolylamino)-1-cyclohexanone (intermediate 3) (57 mg) and isobutylamine (37 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 (8 mg) and a syn-form compound (6 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-b5c4f08c936746c38f6b5276c2bd6094
Source dataset
uspto-grants-2007_05
Patent number
US07217722B2

Linked notes

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