Triethylamine → N-(4-Cyano-1-methyl-piperidin-4-yl)-3-cyclohexyl-2-(3-diethylamino-carbonyl-thioureido)-propionamide

HRID 1005786

Reaction equation

HRID 1005786 reaction equation
Cl.Cl.[NH2:3][CH:4]([CH2:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)[C:5]([NH:7][C:8]1([C:17]#[N:18])[CH2:13][CH2:12][N:11]([CH2:14]CC)[CH2:10][CH2:9]1)=[O:6].[CH2:26]([N:28](CC)[CH2:29][CH3:30])[CH3:27].C(N(CC)[C:36]([S:38][C:39]#[N:40])=[O:37])C>C(#N)C>[C:17]([C:8]1([NH:7][C:5](=[O:6])[CH:4]([NH:3][C:39]([NH:40][N:28]([CH2:29][CH3:30])[CH2:26][CH3:27])=[S:38]=[C:36]=[O:37])[CH2:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]1)#[N:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 22063149N,N-Diethyl carbamoyl thiocyanateHCID 865852002-amino-N-(-4-cyano-1-propyl-piperidin-4-yl)-3-cyclohexylpropionamide bis hydrochloride salt

Product 1

HCID 86596454N-(4-Cyano-1-methyl-piperidin-4-yl)-3-cyclohexyl-2-(3-diethylamino-carbonyl-thioureido)-propionamideYield 49%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 2-amino-N-(-4-cyano-1-propyl-piperidin-4-yl)-3-cyclohexylpropionamide bis hydrochloride salt (560 mg, 1.53 mmol) and triethylamine (500 μL, 3.59 mmol) in acetonitrile (4 mL) was treated with a solution of N,N-diethyl carbamoyl thiocyanate in acetonitrile (3.0 mL, 2.7 mmol). The reaction mixture was stirred overnight at room temperature and concentrated on a rotary evaporator. The resulting residue was chromatographed (ethyl acetate: hexanes 1:1 then ethyl acetate and finally methanol: methylene chloride 1:9 as the eluant) to provide the desired product as a light yellow solid (340 mg, 49%). MS, m/z 451.3=M+1.

Workup

  1. concentrationconcentrated on a rotary evaporator
  2. customThe resulting residue was chromatographed (ethyl acetate: hexanes 1:1

Sources & evidence

ORD record
ord-4a9bf0856b354ea68f6e24148eeae038
Source dataset
uspto-grants-2004_09
Patent number
US06787540B2

Linked notes

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