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

HRID 1093788Notes

Reaction equation

HRID 1093788 reaction equation
C[CH2:2][N:3](C(C)C)C(C)C.C([C:12]1[CH:13]=[C:14]([N:18]2[CH:22]=[C:21]([C:23]([OH:25])=O)[N:20]=[N:19]2)[CH:15]=[CH:16][CH:17]=1)#N.NC1C=C(C=CC=1)C#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:14]2[CH:13]=[CH:12][CH:17]=[CH:16][C:15]=2[C:2]#[N:3])[CH:22]=1)=[O:25]

Participants

9

Reactant 6

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 167023-AminobenzonitrileHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 665915472-Amino-1-[4-(3-trifluoromethyl-phenoxy)-piperidin-1-yl]-ethanone hydrochlorideHCID 665916031-(3-cyano-phenyl)-1H-[1,2,3]triazole-4-carboxylic acid

Product 1

HCID 57874452HCID 57874452, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (61 mg, 4.7 mmol) was added to a stirred solution of 1-(3-cyano-phenyl)-1H-[1,2,3]triazole-4-carboxylic acid (202 mg, 0.94 mmol) (prepared by the method used for the synthesis of Intermediate 64, starting from 3-aminobenzonitrile) in DMF (5 mL) followed by HOBt (14 mg, 1.03 mmol) and EDCI (452 mg, 2.36 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) (351 mg, 1.03 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 75 mg (16% 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, 99.08%. 1H NMR (300 MHz, DMSO-d6): δ 9.48 (s, 1H), 8.58 (t, 2H), 8.4 (d, 1H), 8.06 (d, 1H), 7.9 (t, 1H), 7.38 (t, 3H), 4.9 (m, 1H), 4.3 (d, 2H), 4.0 (s, 1H), 3.8 (s, 1H), 3.5 (m, 2H), 2.1 (t, 2H), 1.8 (s, 1H), 1.6 (s, 1H).

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-a9372ba5f02c44a7b9f63e8987a828e3
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

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