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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 5-Phenyl-pyridine-2-carboxylic acid {2-[4-(5-fluoro-2-trifluoromethyl-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-amide

HRID 1177943
Notes
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Reaction equation

HRID 1177943 reaction equation
CCN(C(C)C)C(C)C.[C:10]1([C:16]2[CH:17]=[CH:18][C:19]([C:22]([NH:24][CH2:25][C:26]([OH:28])=O)=[O:23])=[N:20][CH:21]=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.[F:51][C:52]1[CH:53]=[CH:54][C:55]([C:66]([F:69])([F:68])[F:67])=[C:56]([C:58]([N:60]2[CH2:65][CH2:64][NH:63][CH2:62][CH2:61]2)=[O:59])[CH:57]=1>CN(C=O)C.O>[F:51][C:52]1[CH:53]=[CH:54][C:55]([C:66]([F:68])([F:67])[F:69])=[C:56]([CH:57]=1)[C:58]([N:60]1[CH2:61][CH2:62][N:63]([C:26](=[O:28])[CH2:25][NH:24][C:22]([C:19]2[CH:18]=[CH:17][C:16]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)=[CH:21][N:20]=2)=[O:23])[CH2:64][CH2:65]1)=[O:59]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 57874442[(5-Phenyl-pyridine-2-carbonyl)-amino]-acetic acidHCID 66625607(2-Trifluoromethyl-5-fluoro-phenyl)-piperazin-1-yl-methanone hydrochloride

Product 1

HCID 25165328
5-Phenyl-pyridine-2-carboxylic acid {2-[4-(5-fluoro-2-trifluoromethyl-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-amide
Yield 39%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (151 mg, 0.2 mL, 1.17 mmol) was added to a stirred solution of [(5-phenyl-pyridine-2-carbonyl)-amino]-acetic acid (100 mg, 0.39 mmol) in DMF (2 mL). HOBT (63 mg, 0.46 mmol) and EDCI (89 mg, 0.46 mmol) were then added at room temperature. After 2 minutes, (5-fluoro-2-trifluoromethyl-phenyl)-piperazin-1-yl-methanone hydrochloride salt (146 mg, 0.46 mmol) was added and the resulting mixture was stirred at room temperature overnight. Cold water was then added and the product was extracted with EtOAc and the organic layer was washed with brine. The organic phase was dried over Na2SO4 and concentrated under reduced pressure to afford 78 mg (39% yield) of 5-phenyl-pyridine-2-carboxylic acid {2-[4-(5-fluoro-2-trifluoromethyl-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-amide. LCMS Purity: 95.81%. 1H NMR (DMSO-d6): δ 9 (s, 1H), 8.8 (bt, 1H), 8.3 (d, 1H), 8.1 (m, 1H), 7.9 (m, 1H), 7.8 (d, 1H), 7.6-7.4 (m, 5H), 4.4-4.2 (dd, 2H), 3.8-3.4 (m, 6H), 3.3-3.1 (m, 2H).

Workup

  1. extractionthe product was extracted with EtOAc
  2. washthe organic layer was washed with brine
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5b9f3f7dab2f4136ba8c2cacb9abc95a
Source dataset
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07842696B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes