Diisopropylethylamine → HCID 59853086, compound

HRID 1670266Notes

Reaction equation

HRID 1670266 reaction equation
[F:1][C:2]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[CH:7][C:6]=1/[CH:11]=[CH:12]/[C:13]([OH:15])=O.[CH3:23][C:24]([O:27][C:28]([NH:30][CH:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1)=[O:29])([CH3:26])[CH3:25].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C.CCOC(C)=O>[F:1][C:2]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[CH:7][C:6]=1/[CH:11]=[CH:12]/[C:13]([N:34]1[CH2:33][CH2:32][CH:31]([NH:30][C:28](=[O:29])[O:27][C:24]([CH3:25])([CH3:23])[CH3:26])[CH2:36][CH2:35]1)=[O:15]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 7238334-(N-Boc-amino)piperidineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 59853081HCID 59853081, compound

Product 1

HCID 59853086HCID 59853086, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (E)-3-(4-(2-fluoro-4-nitrophenoxy)pyridin-3-yl)acrylic acid (143 mg, 0.42 mmol), 4-N-Boc-aminopiperidine (Aldrich, 84 mg, 0.42 mmol) in DMF (1.5 mL) was treated with DIPEA (160 μL, 0.92 mmol), and TBTU (160 mg, 0.50 mmol) and the mixture stirred at rt for 2 h. The mixture was diluted with EtOAc, washed with saturated aq. NaHCO3 solution and brine, dried (MgSO4) and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel eluting first with 30-100% EtOAc/hexanes then 5% MeOH/CH2Cl2 to give the title compound (110 mg, 54%) as a light brown solid. 1H NMR (DMSO-d6) δ 9.15 (s, 1H), 8.48 (d, 1H, J=5.6 Hz), 8.44 (dd, 1H, J=2.5, 10.5 Hz), 8.18 (d, 1H, J=9.2 Hz), 7.69 (d, 1H, J=15.3 Hz), 7.58 (dd, 1H, J=8.6, 8.6 Hz), 7.50 (d, 1H, J=15.7 Hz), 6.97 (d, 1H, J=5.6 Hz), 6.89 (d, 1H, J=7.6 Hz), 4.31-4.16 (m, 2H), 3.55-3.46 (m, 1H), 3.20-3.14 (m, 1H), 2.83-2.81 (m, 1H), 1.82-1.71 (m, 2H), 1.34-1.18 (m, 2H), 1.37 (s, 9H); MS (ESI+): m/z 431.04 (100) [(M−C4H9)+H]+; m/z 487.10 (90) (M+H)+.

Workup

  1. washwashed with saturated aq. NaHCO3 solution and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by flash chromatography on silica gel eluting first with 30-100% EtOAc/hexanes

Sources & evidence

ORD record
ord-868b759cb12545a98aabafcb42eea084
Source dataset
uspto-grants-2011_08
Patent number
US07989477B2

Reaction notes

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