1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178523548, compound

HRID 1178138Notes

Reaction equation

HRID 1178138 reaction equation
CCN(C(C)C)C(C)C.[Br:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=1[C:18]([N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)=[O:19].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[OH:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][C:49]=1[C:54]1[NH:58][N:57]=[C:56]([C:59]([NH:61][CH2:62][C:63](O)=[O:64])=[O:60])[CH:55]=1>CN(C=O)C.O>[Br:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=1[C:18]([N:20]1[CH2:21][CH2:22][N:23]([C:63](=[O:64])[CH2:62][NH:61][C:59]([C:56]2[CH:55]=[C:54]([C:49]3[CH:50]=[CH:51][CH:52]=[CH:53][C:48]=3[OH:47])[NH:58][N:57]=2)=[O:60])[CH2:24][CH2:25]1)=[O:19]

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 16771590HCID 16771590, compoundHCID 178525880HCID 178525880, compound

Product 1

HCID 178523548HCID 178523548, compoundYield 68.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (100 mg, 0.13 mL, 0.7 mmol) was added to a stirred solution of (2-Bromo-5-fluoro-phenyl)-piperazin-1-yl-methanone; hydrochloride salt (prepared by the method as described above)(68 mg, 0.21 mmol) in DMF (4 mL). HOBT (31 mg, 0.23 mmol) and EDCI (91 mg, 0.47 mmol) were then added at room temperature. After 2 minutes, {[5-(2-Hydroxy-phenyl)-1H-pyrazole-3-carbonyl]-amino}-acetic acid (50 mg, 0.19 mmol) was added and the resulting mixture was stirred at room temperature for 4 hrs. 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 68.5 mg (68.5% yield) 5-(2-Hydroxy-phenyl)-1H-pyrazole-3-carboxylic acid {2-[4-(2-bromo-5-fluoro-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-amide. LCMS Purity: 95.24%. 1H NMR (DMSO-d6): δ 13.4-13.2 (bs, 1H), 10.4-10.2 (bs, 1H), 8.2-8.0 (bs, 1H), 7.8-7.64 (m, 2H), 7.46-7.34 (bs, 1H), 7.34-7.2 (t, 2H), 7.02-6.84 (m, 4H), 4.26-4.1 (bd, 2H), 3.76-3.46 (bt, 6H), 3.24-3.1 (bd, 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-62884ab3942c46228a4a0fc7783aa7e0
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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