1-Hydroxybenzotriazole → HCID 57855665, compound

HRID 1178082Notes

Reaction equation

HRID 1178082 reaction equation
CCN(C(C)C)C(C)C.[CH:10]1([CH2:13][O:14][C:15]2[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=2[C:17]([OH:19])=O)[CH2:12][CH2:11]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[O:46]=[C:47]([N:64]1[CH2:69][CH2:68][NH:67][CH2:66][CH2:65]1)[CH2:48][NH:49][C:50]([C:52]1[CH:57]=[CH:56][C:55]([C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=2)=[CH:54][CH:53]=1)=[O:51]>CN(C=O)C.O>[CH:10]1([CH2:13][O:14][C:15]2[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=2[C:17]([N:67]2[CH2:66][CH2:65][N:64]([C:47](=[O:46])[CH2:48][NH:49][C:50]([C:52]3[CH:57]=[CH:56][C:55]([C:58]4[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=4)=[CH:54][CH:53]=3)=[O:51])[CH2:69][CH2:68]2)=[O:19])[CH2:11][CH2:12]1

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 149555282-(CyclopropylMethoxy)-benzoic acidHCID 57855677Biphenyl-4-carboxylicacid (2-oxo-2-piperazin-1-yl-ethyl)-amide

Product 1

HCID 57855665HCID 57855665, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (149.8 mg, 1.16 mmol) was added to the stirred solution of 2-Cyclopropylmethoxy-benzoic acid (59.4 mg, 0.31 mmol) in DMF (3 mL), HOBt (45.9 mg, 0.34 mmol) and EDCI.HCl (148.1 mg, 0.77 mmol) at room temperature. After 2 minutes biphenyl-4-carboxylicacid (2-oxo-2-piperazin-1-yl-ethyl)-amide (120 mg, 0.37 mmol) was added and the resulting mixture was stirred at room temperature overnight. Cold water was then added, and the resulting precipitate was filtered. The residue was purified by column chromatography (using 60-120 mesh silica gel and 50% EtOAc in hexane as eluent) to afford 40 mg (26.0% yield) of biphenyl-4-carboxylic acid {2-[4-(2-cyclopropylmethoxy-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-amide, LC-MS purity: 92.64%. 1H NMR: (DMSO) δ 8.64 (t, 1H), 7.96 (d, 2H), 7.8-7.7 (q, 3H), 7.54-7.46 (t, 2H), 7.44-7.32 (m, 2H), 7.2 (d, 1H), 7.1-6.94 (m, 2H), 4.2 (d, 2H), 3.9 (d, 1H), 3.7-3.4 (m, 6H), 3.25-3.0 (m, 2H), 1.2 (s, 2H), 0.6 (d, 2H), 0.3 (s, 2H).

Workup

  1. filtrationthe resulting precipitate was filtered
  2. customThe residue was purified by column chromatography (using 60-120 mesh silica gel and 50% EtOAc in hexane as eluent)

Sources & evidence

ORD record
ord-827c346e3c724e6abee800632279b216
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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