1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 57855650, compound

HRID 1177894Notes

Reaction equation

HRID 1177894 reaction equation
CCN(C(C)C)C(C)C.[C:10]1([C:16]2[S:17][C:18]([C:21]([OH:23])=O)=[CH:19][N:20]=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.[NH2:46][CH2:47][C:48]([N:50]1[CH2:55][CH2:54][N:53]([C:56](=[O:67])[C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][C:58]=2[C:63]([F:66])([F:65])[F:64])[CH2:52][CH2:51]1)=[O:49]>CN(C=O)C.C(OCC)(=O)C.O>[O:49]=[C:48]([N:50]1[CH2:51][CH2:52][N:53]([C:56](=[O:67])[C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][C:58]=2[C:63]([F:66])([F:65])[F:64])[CH2:54][CH2:55]1)[CH2:47][NH:46][C:21]([C:18]1[S:17][C:16]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[N:20][CH:19]=1)=[O:23]

Participants

9

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 1390872-Phenyl-5-carboxythiazoleHCID 669531782-Amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone hydrochloride

Product 1

HCID 57855650HCID 57855650, compoundYield 35.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

DIPEA (170 mg, 0.22 mL, 1.31 mmol) was added to a stirred solution of 2-phenyl-thiazole-5-carboxylic acid (90 mg, 0.43 mmol) in DMF (2 mL). HOBT (71 mg, 0.52 mmol) and EDCI (100 mg, 0.52 mmol) were then added at room temperature. After 2 minutes 2-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone hydrochloride salt (185 mg, 0.52 mmol) was added and the resulting mixture was stirred at room temperature overnight. Cold water was then added and then extrated with ethyl acetate. The organic layer was washed with brine and dried over Na2SO4 and concentrated under reduced pressure to afford 77.1 mg (35%) of 2-phenyl-thiazole-5-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide. LCMS Purity: 95.1%. 1H NMR (DMSO-d6): δ 9.0-8.9 (m, 1H), 8.54-8.5 (s, 1H), 8.0 (m, 2H), 7.9-7.64 (m, 3H), 7.6-7.5 (m, 4H), 4.24-4.1 (m, 2H), 3.8-3.6 (m, 4H), 3.5-3.4 (m, 2H), 3.2-3.0 (m, 2H).

Workup

  1. washThe organic layer was washed with brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c22f8b4734f8402ca27391b94efaccc2
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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