Thiopheneethanamine → HCID 17838037, compound

HRID 1352169Notes

Reaction equation

HRID 1352169 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.S1C=CC=C1[CH2:23][CH2:24][NH2:25].[C:26](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:25][CH:24]([CH3:23])[CH3:26])[CH2:13][CH2:12]3)=[CH:7][CH:8]=2)[CH:3]=[N:2]1

Participants

6

Reactant 4

HCID 116521ThiopheneethanamineHCID 5049666Sodium triacetoxyborohydrideHCID 178382714-(1H-5-Indazolylamino)-1-cyclohexanone2×HCID 21893726Hydrochloride methanol

Product 1

HCID 17838037HCID 17838037, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-(1H-5-Indazolylamino)-1-cyclohexanone (intermediate 3) (57 mg) and 2-thiophenethylamine (64 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 (21 mg) and a syn-form compound (14 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-fb37f9ef3b0d465f978e92a66a371e8e
Source dataset
uspto-grants-2007_05
Patent number
US07217722B2

Reaction notes

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