1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 57874401, compound

HRID 1093851Notes

Reaction equation

HRID 1093851 reaction equation
CCN(C(C)C)C(C)C.[C:10]1([N:16]2[CH:20]=[C:19]([C:21]([NH:23][CH2:24][C:25]([OH:27])=O)=[O:22])[N:18]=[N:17]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[NH:50]1[CH2:55][CH2:54][CH:53]([O:56][C:57]2[CH:58]=[C:59]([CH:62]=[CH:63][CH:64]=2)[C:60]#[N:61])[CH2:52][CH2:51]1>CN(C=O)C.O>[C:60]([C:59]1[CH:58]=[C:57]([CH:64]=[CH:63][CH:62]=1)[O:56][CH:53]1[CH2:54][CH2:55][N:50]([C:25](=[O:27])[CH2:24][NH:23][C:21]([C:19]2[N:18]=[N:17][N:16]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:20]=2)=[O:22])[CH2:51][CH2:52]1)#[N:61]

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 43170522HCID 43170522, compoundHCID 534337453-[(Piperidin-4-yl)oxy]benzonitrile--hydrogen chloride (1/1)

Product 1

HCID 57874401HCID 57874401, compoundYield 32.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (167.9 mg, 1.3 mmol) was added to a stirred solution of [(1-phenyl-1H-[1,2,3]triazole-4-carbonyl)-amino]-acetic acid (80 mg, 0.32 mmol) in DMF (3 mL) followed by HOBt (48.2 mg, 0.35 mmol) and EDCI (124.5 mg, 0.65 mmol). After 2 minutes of stirring, 3-(piperidin-4-yloxy)-benzonitrile hydrochloride (prepared by the method used for the synthesis of Intermediate 15) (77.5 mg, 0.32 mmol) was added and the resulting mixture was stirred at room temperature overnight. Cold water was added and precipitate was collected. The solid was purified by column chromatography (using 70% ethyl acetate in hexane as eluent) to afford 45 mg (32.6% Yield) of 1-phenyl-1H-[1,2,3]triazole-4-carboxylic acid {2-[4-(3-cyano-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-amide. LC/MS [M+H]+: 431.18, 85.06%. 1H NMR (300 MHz, DMSO-d6): δ 9.35 (s, 1H), 8.5 (t, 1H), 8.0 (d, 2H), 7.7-7.6 (m, 2H), 7.58-7.45 (m, 3H), 7.45-7.32 (m, 2H), 4.75 (m, 1H), 4.2 (d, 2H), 4.0-3.9 (m, 1H), 3.8-3.7 (m, 1H), 2.1-1.9 (m, 2H), 1.75-1.5 (m, 2H).

Workup

  1. additionwas added
  2. stirringthe resulting mixture was stirred at room temperature overnight
  3. customprecipitate was collected
  4. customThe solid was purified by column chromatography (using 70% ethyl acetate in hexane as eluent)

Sources & evidence

ORD record
ord-af19936c8bea471ca191443122287153
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

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