1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 66591602, compound

HRID 1093859Notes

Reaction equation

HRID 1093859 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]=[CH: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.[CH3:50][C:51]1[CH:58]=[CH:57][C:54]([C:55]#[N:56])=[CH:53][C:52]=1[O:59][CH:60]1[CH2:65][CH2:64][NH:63][CH2:62][CH2:61]1>CN(C=O)C.O>[C:55]([C:54]1[CH:57]=[CH:58][C:51]([CH3:50])=[C:52]([CH:53]=1)[O:59][CH:60]1[CH2:61][CH2:62][N:63]([C:25](=[O:27])[CH2:24][NH:23][C:21]([C:19]2[N:18]=[CH:17][N:16]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:20]=2)=[O:22])[CH2:64][CH2:65]1)#[N:56]

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 66591676HCID 66591676, compoundHCID 66591819[(1-phenyl-1H-imidazole-4-carbonyl)-amino]-acetic acid

Product 1

HCID 66591602HCID 66591602, compoundYield 82.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (236 mg, 1.826 mmol) was added to a stirred solution of [(1-phenyl-1H-imidazole-4-carbonyl)-amino]-acetic acid (prepared from Intermediate 68 by means of Step 3 of the General Scheme) (100 mg, 0.4 mmol) in DMF (5 mL) followed by HOBt (60.5 mg, 0.4 mmol) and EDCI (195 mg, 1.02 mmol). After 2 minutes of stirring, 4-methyl-3-(piperidin-4-yloxy)-benzonitrile hydrochloride (113 mg, 0.45 mmol) (prepared by the method used for the synthesis of Intermediate 15) was added and the resulting mixture was stirred at ambient temperature overnight. The reaction mixture was diluted with cold water, the precipitate was collected and purified by recrystallisation from a mixture of diethyl ether (15 mL) and MeOH (0.1 mL) to afford 149 mg (82.7% Yield) of 1-phenyl-1H-imidazole-4-carboxylic acid {2-[4-(5-cyano-2-methyl-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-amide. LC/MS [M+H]+: 443, 98.73%. 1H NMR (300 MHz, DMSO-d6): δ 8.4 (s, 1H), 8.3 (s, 1H), 8.08 (t, 1H), 7.8 (d, 2H), 7.6 (t, 3H), 7.4-7.18 (m, 3H), 4.85 (m, 1H), 4.2 (d, 2H), 3.85-3.6 (d, 2H), 3.5 (bs, 2H), 2.3 (s, 3H), 2.1 (d, 2H), 1.8 (d, 2H).

Workup

  1. additionwas added
  2. stirringthe resulting mixture was stirred at ambient temperature overnight
  3. customthe precipitate was collected
  4. custompurified by recrystallisation from a mixture of diethyl ether (15 mL) and MeOH (0.1 mL)

Sources & evidence

ORD record
ord-48492faea6dd498ab0531ec8515af3d3
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

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