Diisopropylethylamine → HCID 178465356, compound

HRID 1827844Notes

Reaction equation

HRID 1827844 reaction equation
[CH2:1]([NH:3][C:4]([N:6]=[C:7](OC)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5])[CH3:2].Cl.Cl.[NH2:18][CH:19]([CH2:32][CH:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1)[C:20]([NH:22][C:23]1([C:30]#[N:31])[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]1)=[O:21].C(N(CC)C(C)C)(C)C>CO>[C:30]([C:23]1([NH:22][C:20](=[O:21])[CH:19]([NH:18][C:7](=[N:6][C:4](=[O:5])[NH:3][CH2:1][CH3:2])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:32][CH:33]2[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]2)[CH2:24][CH2:25][N:26]([CH3:29])[CH2:27][CH2:28]1)#[N:31]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 225663392-amino-N-(-4-cyano-1-methyl-piperidin-4-yl)-3-cyclohexylpropionamide bis hydrochloride saltHCID 69416768Methyl N-(ethylcarbamoyl)benzenecarboximidate

Product 1

HCID 178465356HCID 178465356, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1-ethyl-3-(methoxy-phenyl-methylene)-urea (350 mg, 1.70 mmol), 2-amino-N-(4-cyano-1-methyl-piperidin-4-yl)-3-cyclohexyl-propionamide bis hydrochloride salt (512 mg, 1.40 mmol) and N,N-diisopropylethylamine (352 mg, 2.73 mmol) in dry methanol (5.0 mL) was stirred at room temperature for 60 h. The reaction mixture was concentrated and the resulting residue was chromatographed over 50 g of flash silica gel using dichloromethane to 5% methanol in dichloromethane as the eluant. This provided the desired product as a light yellow solid (280 mg, 43%) which was further purified by HPLC using a 20×250 mm C18 reverse phase column with the method being 20% acetonitrile in water to 90% acetonitrile in water. MS, m/z 467=M+1.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe resulting residue was chromatographed over 50 g of flash silica gel

Sources & evidence

ORD record
ord-f1475bf665c24030ac1021d15ea750bb
Source dataset
uspto-grants-2006_06
Patent number
US07056915B2

Reaction notes

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