1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 59559649, compound

HRID 1178004Notes

Reaction equation

HRID 1178004 reaction equation
CCN(C(C)C)C(C)C.[CH2:10]([O:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([OH:24])=O)=[CH:20][CH:19]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[NH2:48][CH:49]([CH3:70])[C:50]([N:52]1[CH2:57][CH2:56][N:55]([C:58](=[O:69])[C:59]2[CH:64]=[CH:63][CH:62]=[CH:61][C:60]=2[C:65]([F:68])([F:67])[F:66])[CH2:54][CH2:53]1)=[O:51]>CN(C=O)C.O>[CH2:10]([O:17][C:18]1[CH:19]=[CH:20][C:21]([C:22]([NH:48][CH:49]([CH3:70])[C:50](=[O:51])[N:52]2[CH2:53][CH2:54][N:55]([C:58](=[O:69])[C:59]3[CH:64]=[CH:63][CH:62]=[CH:61][C:60]=3[C:65]([F:66])([F:68])[F:67])[CH2:56][CH2:57]2)=[O:24])=[CH:25][CH:26]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 738804-(Benzyloxy)benzoic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 66953605HCID 66953605, compound

Product 1

HCID 59559649HCID 59559649, compoundYield 48.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (131 mg, 0.17 mL, 0.76 mmol) was added to a stirred solution of 4-Benzyloxy-benzoic acid (58 mg, 0.25 mmol) in DMF (2 mL). HOBT (41 mg, 0.3 mmol) and EDCI (58 mg, 0.3 mmol) were then added at room temperature. After 2 minutes, 2-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-propan-1-one (85 mg, 0.25 mmol) 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 60-120 silica gel and 10% MeOH in CHCl3 as eluent) to afford 65 mg (47% yield) of 4-benzyloxy-N-{1-methyl-2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-benzamide. LCMS Purity: 95%. 1H NMR (CDCl3): δ 7.76 (m, 3H), 7.6 (m, 2H), 7.4-7.3 (m, 5H), 7.1 (d, 1H), 7.0 (d, 2H), 5.22 (s, 2H), 4.2 (d, 1H), 3.82 (m, 2H), 3.7-3.4.(m, 6H), 2.0 (m, 1H), 1.4 (dd, 3H).

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
  5. customto get the residue
  6. customThe obtained residue was purified by column chromatography (using 60-120 silica gel and 10% MeOH in CHCl3 as eluent)

Sources & evidence

ORD record
ord-4fc9978781f2421da258fdabffe976e7
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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