1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 57874452, compound

HRID 1093787Notes

Reaction equation

HRID 1093787 reaction equation
CCN(C(C)C)C(C)C.[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N:18]1[CH:22]=[C:21]([C:23]([OH:25])=O)[N:20]=[N:19]1)#[N:11].NC1C=CC=CC=1C#N.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[NH2:57][CH2:58][C:59]([N:61]1[CH2:66][CH2:65][CH:64]([O:67][C:68]2[CH:73]=[CH:72][CH:71]=[C:70]([C:74]([F:77])([F:76])[F:75])[CH:69]=2)[CH2:63][CH2:62]1)=[O:60]>CN(C=O)C.O>[O:60]=[C:59]([N:61]1[CH2:62][CH2:63][CH:64]([O:67][C:68]2[CH:73]=[CH:72][CH:71]=[C:70]([C:74]([F:77])([F:75])[F:76])[CH:69]=2)[CH2:65][CH2:66]1)[CH2:58][NH:57][C:23]([C:21]1[N:20]=[N:19][N:18]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[C:10]#[N:11])[CH:22]=1)=[O:25]

Participants

9

Reactant 6

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 729132-AminobenzonitrileHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 665915472-Amino-1-[4-(3-trifluoromethyl-phenoxy)-piperidin-1-yl]-ethanone hydrochlorideHCID 665916151-(2-Cyanophenyl)-1H-1,2,3-triazole-4-carboxylic acid

Product 1

HCID 57874452HCID 57874452, compoundYield 37.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (163 mg, 1.26 mmol) was added to a stirred solution of 1-(2-cyano-phenyl)-1H-[1,2,3]triazole-4-carboxylic acid (60 mg, 0.28 mmol) (prepared by the method used for the synthesis of Intermediate 64, starting from 2-aminobenzonitrile) in DMF (5 mL) followed by HOBt (41 mg, 0.3 mmol) and EDCI (134 mg, 0.7 mmol). After 2 minutes of stirring, 2-amino-1-[4-(3-trifluoromethyl-phenoxy)-piperidin-1-yl]-ethanone hydrochloride (prepared according to Step 1 and 5 of the General Scheme) (104 mg, 0.3 mmol) was added and the resulting mixture was stirred at ambient temperature overnight. Cold water was then added and the solid was collected. The solid obtained was purified by column chromatography (using 60-120 silica gel and 30-70% EtOAc in hexane as eluent) to afford 52 mg (37.6% Yield) of 1-(2-cyano-phenyl)-1H-[1,2,3]triazole-4-carboxylic acid {2-oxo-2-[4-(3-trifluoromethyl-phenoxy)-piperidin-1-yl]-ethyl}-amide. LC/MS [M+H]+: 499, 96.38%. 1H NMR (300 MHz, DMSO-d6): δ 9.3 (s, 1H), 8.64 (t, 1H), 8.22 (d, 1H), 8.02 (t, 2H), 7.84 (t, 1H), 7.6 (t, 1H), 7.4 (t, 3H), 4.9 (m, 1H), 4.3 (d, 2H), 4.0 (s, 1H), 3.8 (s, 1H), 3.5 (s, 1H), 2.1 (t, 2H), 1.8 (d, 2H).

Workup

  1. customprepared by the method
  2. additionwas added
  3. stirringthe resulting mixture was stirred at ambient temperature overnight
  4. customthe solid was collected
  5. customThe solid obtained
  6. customwas purified by column chromatography (using 60-120 silica gel and 30-70% EtOAc in hexane as eluent)

Sources & evidence

ORD record
ord-4c7fda6c921e44db923404d0887b3696
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

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