1-Hydroxybenzotriazole → HCID 44231329, compound

HRID 1665638Notes

Reaction equation

HRID 1665638 reaction equation
C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[O:20]=[C:21]([N:26]1[CH2:31][CH2:30][N:29]([C:32](=[O:43])[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[C:39]([F:42])([F:41])[F:40])[CH2:28][CH2:27]1)[CH2:22][C:23]([OH:25])=O.CCN=C=NCCCN(C)C.Cl.[N:56]1([C:62]2[CH:67]=[CH:66][C:65]([NH2:68])=[CH:64][CH:63]=2)[CH2:61][CH2:60][CH2:59][CH2:58][CH2:57]1>CN(C=O)C.O>[O:20]=[C:21]([N:26]1[CH2:27][CH2:28][N:29]([C:32](=[O:43])[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[C:39]([F:42])([F:41])[F:40])[CH2:30][CH2:31]1)[CH2:22][C:23]([NH:68][C:65]1[CH:64]=[CH:63][C:62]([N:56]2[CH2:61][CH2:60][CH2:59][CH2:58][CH2:57]2)=[CH:67][CH:66]=1)=[O:25]

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 4135014-(Piperidin-1-yl)anilineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 578758113-Oxo-3-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-propionic acid

Product 1

HCID 44231329HCID 44231329, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
10 °C

Procedure

HOBt (43 mg, 0.31 mmol) and DIEA (150 mg, 1.1 mmol) were added to a stirred solution of 3-oxo-3-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-propionic acid (100 mg, 0.29 mmol) in DMF. The reaction mixture was cooled to 10° C. and EDCI.HCl (111 mg, 0.58 mmol) followed by 4-piperidin-1-yl-phenylamine (61.4 mg, 0.34 mmol) were added. The reaction mixture was stirred at room temperature overnight then diluted with water and the product extracted with ethyl acetate. The ethyl acetate layer was washed with brine solution, dried over Na2SO4 and concentrated. The residue was purified by column chromatography using silica gel 60-120 mesh (80% ethyl acetate in hexane) to afford 69 mg (47%) of. LCMS: 503.22 (M+1)+, 94.4%, 1H NMR: (CDCl3): δ 9.3 (d, 1H), 7.8 (d, 1H), 7.7 (m, 2H), 7.5 (m, 3H), 7.0 (d, 2H), 4.5 (s, 1H), 4.1-3.8 (m, 2H), 3.8-3.6 (m, 3H), 3.6-3.4 (m, 3H), 3.3-3.2 (m, 2H), 3.1 (t, 4H), 1.9-1.7 (m, 7H), 1.6 (q, 2H).

Workup

  1. additionwere added
  2. extractionthe product extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with brine solution
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography
  7. customto afford 69 mg (47%) of

Sources & evidence

ORD record
ord-516f45b7f53c4f9791b5754ddb8a1b19
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Reaction notes

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