1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178523537, compound

HRID 1177921Notes

Reaction equation

HRID 1177921 reaction equation
CCN(C(C)C)C(C)C.[F:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]1[NH:21][N:20]=[C:19]([C:22]([OH:24])=O)[CH:18]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[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.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:22]([C:19]1[CH:18]=[C:17]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[F:10])[NH:21][N:20]=1)=[O:24]

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 595596292-Amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanoneHCID 178524114HCID 178524114, compound

Product 1

HCID 178523537HCID 178523537, compoundYield 92.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (92 mg, 0.12 mL, 0.71 mmol) was added to a stirred solution of 5-(2-fluoro-phenyl)-1H-pyrazole-3-carboxylic acid (59 mg, 0.28 mmol) in DMF (2 mL). HOBT (40 mg, 0.29 mmol) and EDCI (57 mg, 0.29 mmol) were then added at room temperature. After 2 minutes, 2-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone (100 mg, 0.28 mmol) was added and the resulting mixture was stirred at room temperature overnight. Cold water was then added and filtered the solid precipitated to afford 131 mg (91.6% yield) of 5-(2-fluoro-phenyl)-1H-pyrazole-3-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide. LCMS Purity: 95.28%. 1H NMR (DMSO-d6): δ 13.8 (d, 1H), 8.0 (m, 1H), 7.6 (m, 3H), 7.2 (m, 4H), 7.1 (m, 1H), 4.1 (d, 2H), 3.5 (m, 4H), 3.35 (m, 2H), 3.0 (m, 2H).

Workup

  1. filtrationfiltered the solid
  2. customprecipitated

Sources & evidence

ORD record
ord-2d8d51bfd802498bafcb81736775b2e4
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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