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1-Hydroxybenzotriazole → HCID 44235961, compound

HRID 1093596
Notes
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Reaction equation

HRID 1093596 reaction equation
[C:1]1([NH:7][C:8]2[CH:20]=[CH:19][C:11]([C:12]([NH:14][CH2:15][C:16]([OH:18])=O)=[O:13])=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.FC(F)(F)C(O)=O.[Br:59][C:60]1[CH:72]=[CH:71][CH:70]=[CH:69][C:61]=1[O:62][CH:63]1[CH2:68][CH2:67][NH:66][CH2:65][CH2:64]1>CN(C=O)C.O>[Br:59][C:60]1[CH:72]=[CH:71][CH:70]=[CH:69][C:61]=1[O:62][CH:63]1[CH2:68][CH2:67][N:66]([C:16](=[O:18])[CH2:15][NH:14][C:12](=[O:13])[C:11]2[CH:10]=[CH:9][C:8]([NH:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:20][CH:19]=2)[CH2:65][CH2:64]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57874498(4-Phenylamino-benzoylamino)-acetic acidHCID 66591525HCID 66591525, compound

Product 1

HCID 44235961
HCID 44235961, compound
Yield 32.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of (4-phenylamino-benzoylamino)-acetic acid (0.087 g, 0.00032 mol) in DMF (5 mL) was added DIPEA (0.104 g, 0.00081 mol), HOBt (0.043 g, 0.00032 mol) and EDCI.HCl (0.061 g, 0.00032 mol) at ambient temperature. After 2 minutes 4-(2-bromo-phenoxy)-piperidine trifluoroacetate (0.1 g, 0.00027 mol) and the resulting mixture was stirred overnight. The reaction mixture was then diluted with cold water and the product was extracted with ethyl acetate. The organic layer was washed with brine solution and dried over sodium sulfate. The organic layer was collected and concentrated under reduced pressure to afford 0.045 g (32%) of N-{2-[4-(2-bromo-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-4-phenylamino-benzamide. LCMS: 508.12 (M+1)+, 96.85%, 1H NMR (DMSO-d6): δ 8.6 (s, 1H), 8.3 (t, 1H), 7.8 (d, 2H), 7.6 (dd, 1H), 7.3 (m, 4H), 7.2 (d, 2H), 7.1 (d, 2H), 6.9 (q, 2H), 4.8 (m, 1H), 4.2 (t, 2H), 3.7 (m, 2H), 3.5 (m, 2H), 2.0 (m, 2H), 1.7 (m, 2H).

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. washThe organic layer was washed with brine solution
  3. dry with materialdried over sodium sulfate
  4. customThe organic layer was collected
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-addbb51e0809430b8bf7fcfaa26f2d95
Source dataset
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08129376B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes