1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178523556, compound

HRID 1093853Notes

Reaction equation

HRID 1093853 reaction equation
CCN(C(C)C)C(C)C.[C:10]1([C:16]2[NH:20][N:19]=[C:18]([C:21]([NH:23][CH2:24][C:25]([OH:27])=O)=[O:22])[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.[F:50][C:51]([F:64])([F:63])[C:52]1[CH:53]=[C:54]([CH:60]=[CH:61][CH:62]=1)[O:55][CH:56]1[CH2:59][NH:58][CH2:57]1>CN(C=O)C.O>[O:27]=[C:25]([N:58]1[CH2:59][CH:56]([O:55][C:54]2[CH:60]=[CH:61][CH:62]=[C:52]([C:51]([F:50])([F:64])[F:63])[CH:53]=2)[CH2:57]1)[CH2:24][NH:23][C:21]([C:18]1[CH:17]=[C:16]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:20][N:19]=1)=[O:22]

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 510516403-[3-(Trifluoromethyl)phenoxy]-azetidine hydrochlorideHCID 178525878HCID 178525878, compound

Product 1

HCID 178523556HCID 178523556, compoundYield 51.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (158.2 mg, 1.22 mmol) was added to a stirred solution of [(5-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetic acid (75 mg, 0.30 mmol) in DMF (2 mL) followed by HOBt (43.4 mg, 0.32 mmol) and EDCI (61.6 mg, 0.32 mmol). After 2 minutes of stirring, 3-(3-trifluoromethyl-phenoxy)-azetidine hydrochloride (77.5 mg, 0.3 mmol) was added and the resulting mixture was stirred at room temperature overnight. Cold water was added followed by extraction with ethyl acetate. The organic phase was dried over sodium sulfate and concentrated under reduced pressure to afford the residue. The residue was purified by column chromatography (using silica gel 60- and 100% ethyl acetate as eluent) to afford 69 mg (51.1% Yield) of 5-phenyl-1H-pyrazole-3-carboxylic acid {2-oxo-2-[3-(3-trifluoromethyl-phenoxy)-azetidin-1-yl]-ethyl}-amide. LC/MS [M+H]+: 445.14, 90.72%. 1H NMR (300 MHz, DMSO-d6): δ 14.8 (s, 1H), 8.2 (t, 1H), 7.78 (t, 2H), 7.5 (t, 1H), 7.3 (m, 5H), 7.16 (d, 2H), 7.1 (d, 1H), 5.18 (m, 1H), 4.64 (q, 1H), 4.36 (m, 1H), 4.18 (m, 1H), 3.84 (m, 3H).

Workup

  1. stirringthe resulting mixture was stirred at room temperature overnight
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto afford the residue
  6. customThe residue was purified by column chromatography (using silica gel 60- and 100% ethyl acetate as eluent)

Sources & evidence

ORD record
ord-c5660b7cdd7946d1b6c4f93f8c45272b
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

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