1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178523545, compound

HRID 1177887Notes

Reaction equation

HRID 1177887 reaction equation
CCN(C(C)C)C(C)C.[OH:10][C:11]1[N:12]=[CH:13][C:14]([C:17]([OH:19])=O)=[N:15][CH:16]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[NH2:42][CH2:43][C:44]([N:46]1[CH2:51][CH2:50][N:49]([C:52](=[O:63])[C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=2[C:59]([F:62])([F:61])[F:60])[CH2:48][CH2:47]1)=[O:45]>CN(C=O)C>[O:45]=[C:44]([N:46]1[CH2:47][CH2:48][N:49]([C:52](=[O:63])[C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=2[C:59]([F:62])([F:61])[F:60])[CH2:50][CH2:51]1)[CH2:43][NH:42][C:17]([C:14]1[CH:13]=[N:12][C:11]([OH:10])=[CH:16][N:15]=1)=[O:19]

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 669531782-Amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone hydrochlorideHCID 1785247745-Hydroxypyrazine-2-carboxylic acid

Product 1

HCID 178523545HCID 178523545, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

DIPEA (553 mg, 0.732 mL, 4.28 mmol) was added to a stirred solution of 5-hydroxy-pyrazine-2-carboxylic acid (200 mg, 1.42 mmol) in DMF (3 mL). HOBT (231 mg, 1.71 mmol) and EDCI (328 mg, 1.71 mmol) were then added at room temperature. After 2 minutes 2-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone hydrochloride salt (600 mg, 1.71 mmol) was added and the resulting mixture was stirred at room temperature overnight. The reaction mixture was concentrated, methanol was then added, filtered the solid precipitated. The solid obtained was purified by column chromatography (using silica gel of 60-120 mesh and 10% MeOH in CHCl3 as eluent) to afford 205 mg (32.85%) of 5-hydroxy-pyrazine-2-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide. LCMS Purity: 91.22%. 1H NMR (DMSO-d6): δ 8.3 (bt, 1H), δ 8.0 (m, 2H), 7.9-7.76 (m, 2H), 7.7 (m, 1H), 7.6-7.5 (d, 2H), 4.26-4.1 (dd, 2H), 3.8-3.68 (m, 2H), 3.6-3.5 (m, 2H), 3.4 (m, 2H), δ 3.2-3.0 (m, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionmethanol was then added
  3. filtrationfiltered the solid
  4. customprecipitated
  5. customThe solid obtained
  6. customwas purified by column chromatography (using silica gel of 60-120 mesh and 10% MeOH in CHCl3 as eluent)

Sources & evidence

ORD record
ord-ae365842481c4965821f54f5226be3f2
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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