1-Hydroxybenzotriazole → HCID 57855663, compound

HRID 1178090Notes

Reaction equation

HRID 1178090 reaction equation
CCN(C(C)C)C(C)C.[F:10][C:11]([F:22])([F:21])[C:12]1[C:17]([C:18]([OH:20])=O)=[CH:16][N:15]=[CH:14][CH:13]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[O:45]=[C:46]([N:63]1[CH2:68][CH2:67][NH:66][CH2:65][CH2:64]1)[CH2:47][NH:48][C:49]([C:51]1[CH:56]=[CH:55][C:54]([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)=[CH:53][CH:52]=1)=[O:50]>CN(C=O)C.O>[O:45]=[C:46]([N:63]1[CH2:68][CH2:67][N:66]([C:18]([C:17]2[CH:16]=[N:15][CH:14]=[CH:13][C:12]=2[C:11]([F:10])([F:22])[F:21])=[O:20])[CH2:65][CH2:64]1)[CH2:47][NH:48][C:49]([C:51]1[CH:52]=[CH:53][C:54]([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)=[CH:55][CH:56]=1)=[O:50]

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27775493-Pyridinecarboxylic acid, 4-(trifluoromethyl)-HCID 57855677Biphenyl-4-carboxylicacid (2-oxo-2-piperazin-1-yl-ethyl)-amide

Product 1

HCID 57855663HCID 57855663, compoundYield 47.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (149.8 mg, 1.15 mmol) was added to a stirred solution of 4-trifluoromethyl-nicotinic acid (49.2 mg, 0.26 mmol) in DMF (3 mL), HOBt (38.2 mg, 0.28 mmol) and EDCI.HCl (123.4 mg, 0.64 mmol) at room temperature. After 2 minutes biphenyl-4-carboxylicacid (2-oxo-2-piperazin-1-yl-ethyl)-amide (100 mg, 0.31 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 80% EtOAc in hexane as eluent) to afford 48 mg (47.6% yield) of biphenyl-4-carboxylicacid {2-oxo-2-[4-(4-trifluoromethyl-pyridine-3-carbonyl)-piperazin-1-yl]-ethyl}-amide, LC-MS purity: 94.74%, 1H NMR: (DMSO) δ 9.0-8.84 (d, 2H), 8.7-8.6 (t, 1H), 8.0 (d, 2H), 7.9 (d, 1H), 7.84-7.7 (q, 4H), 7.6-7.4 (m, 3H) 4.2 (d, 2H), 3.8-3.6 (d, 4H), 3.3-3.2 (s, 4H).

Workup

  1. filtrationthe resulting precipitate was filtered
  2. customThe residue was purified by column chromatography (using 60-120 mesh silica gel and 80% EtOAc in hexane as eluent)

Sources & evidence

ORD record
ord-d683213ce6a84ebebf0de9c49e83736f
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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