1-Hydroxybenzotriazole → HCID 44231208, compound

HRID 1665616Notes

Reaction equation

HRID 1665616 reaction equation
C1C=CC2N(O)N=NC=2C=1.[O:11]=[C:12]([N:17]1[CH2:22][CH2:21][N:20]([C:23](=[O:34])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[C:30]([F:33])([F:32])[F:31])[CH2:19][CH2:18]1)[CH2:13][C:14]([OH:16])=O.CCN=C=NCCCN(C)C.Cl.[C:47]1([C:53]2[CH:54]=[CH:55][C:56]([NH2:59])=[N:57][CH:58]=2)[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1>CN(C1C=CN=CC=1)C.CN(C=O)C.O>[O:11]=[C:12]([N:17]1[CH2:18][CH2:19][N:20]([C:23](=[O:34])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[C:30]([F:33])([F:32])[F:31])[CH2:21][CH2:22]1)[CH2:13][C:14]([NH:59][C:56]1[CH:55]=[CH:54][C:53]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)=[CH:58][N:57]=1)=[O:16]

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 1050975-Phenyl-2-pyridinamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 578758113-Oxo-3-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-propionic acid

Product 1

HCID 44231208HCID 44231208, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
10 °C

Procedure

HOBt (57 mg, 0.42 mmol) and DMAP (46 mg, 0.38 mmol) were added to a stirred solution of 3-oxo-3-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-propionic acid (60 mg, 0.35 mmol) in DMF (2 mL). The reaction mixture was cooled to 10° C. and EDCI.HCl (81 mg, 0.42 mmol) followed by 5-phenyl-pyridin-2-ylamine (120 mg, 0.35 mmol) were added. The reaction mixture was stirred at the room temperature overnight, then diluted with water and the product extracted with ethyl acetate. The ethyl acetate was washed with brine solution, dried over Na2SO4 and evaporated. The residue was purified by column chromatography using silica gel 60-120 mesh and 80% ethyl acetate in hexane as the eluant to afford 65 mg (38% 0 of 3-oxo-N-(5-phenyl-pyridin-2-yl)-3-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-propionamide. LCMS: 497.18 (M+1)+, 90.4%, 1H NMR: (CDCl3): δ 9.6 (d, 1H), 8.5 (s, 1H), 8.2 (m, 1H), 7.9 (m, 1H), 7.75 (d, 1H), 7.6 (m, 4H), 7.45 (t, 2H), 7.35 (m, 2H), 4.0 (m, 2H), 3.7 (m, 3H), 3.55 (m, 4H), 3.26 (m, 2H).

Workup

  1. additionwere added
  2. extractionthe product extracted with ethyl acetate
  3. washThe ethyl acetate was washed with brine solution
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-9ce614309ead4693bd855573b604e708
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Reaction notes

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