1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 25166707, compound

HRID 1177910Notes

Reaction equation

HRID 1177910 reaction equation
CCN(C(C)C)C(C)C.Cl.[NH2:11][CH2:12][C:13]([N:15]1[CH2:20][CH2:19][N:18]([C:21](=[O:32])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:28]([F:31])([F:30])[F:29])[CH2:17][CH2:16]1)=[O:14].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[S:54]1[C:58]([C:59]2[CH:67]=[CH:66][C:62]([C:63](O)=[O:64])=[CH:61][CH:60]=2)=[CH:57][N:56]=[CH:55]1>CN(C=O)C.O>[O:14]=[C:13]([N:15]1[CH2:16][CH2:17][N:18]([C:21](=[O:32])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:28]([F:31])([F:29])[F:30])[CH2:19][CH2:20]1)[CH2:12][NH:11][C:63](=[O:64])[C:62]1[CH:61]=[CH:60][C:59]([C:58]2[S:54][CH:55]=[N:56][CH:57]=2)=[CH:67][CH:66]=1

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 669531424-(5-Thiazolyl)benzoic acidHCID 669531782-Amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone hydrochloride

Product 1

HCID 25166707HCID 25166707, compoundYield 45.33%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (232 mg, 0.31 mL, 1.79 mmol) was added to a stirred solution of 2-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone hydrochloride salt (prepared by the method as described above) (190 mg, 0.54 mmol) in DMF (3 mL). HOBT (67 mg, 0.49 mmol) and EDCI (172 mg, 0.89 mmol) were then added at room temperature. After 2 minutes, 4-thiazol-5-yl-benzoic acid (100 mg, 0.49 mmol) (prepared by the method described above) 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 get the residue. The obtained residue was purified by column chromatography (using silica gel of 60-120 mesh and 70% EtOAc in Hexane as eluent) to afford 102 mg (45.33% yield) N-{2-Oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-4-thiazol-5-yl-benzamide. LCMS Purity: 97.53%. 1H NMR (CDCl3): δ 8.8 (s, 1H), 8.16 (s, 1H), 7.92-7.84 (d, 2H), 7.78-7.72 (d, 1H), 7.7-7.52 (m, 4H), 7.38-7.3 (d, 2H), 4.36-4.3 (m, 1H), 4.28-4.2 (m, 1H), 4.1-4.0 (d, 2H), 3.98-3.88 (m, 1H), 3.8-3.64 (m, 2H), 3.64-3.5 (d, 2H), 3.44-3.18 (t, 1H), 3.3-3.21 (bs, 2H).

Workup

  1. customprepared by the method
  2. additionwas added
  3. extractionthe product was extracted with EtOAc
  4. washthe organic layer was washed with brine
  5. dry with materialThe organic phase was dried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customto get the residue
  8. customThe obtained residue was purified by column chromatography (using silica gel of 60-120 mesh and 70% EtOAc in Hexane as eluent)

Sources & evidence

ORD record
ord-581d07783ea747c1be12aae3a61335e1
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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