Triphenylphosphine → HCID 11554163, compound

HRID 552166Notes

Reaction equation

HRID 552166 reaction equation
[CH:1]1([CH2:4][CH2:5][NH:6][C:7]([C:9]2[N:10]=[N:11][C:12]([N:15]3[CH2:20][CH2:19][CH:18]([CH2:21][OH:22])[CH2:17][CH2:16]3)=[CH:13][CH:14]=2)=[O:8])[CH2:3][CH2:2]1.O[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C:30]([F:33])([F:32])[F:31].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH:1]1([CH2:4][CH2:5][NH:6][C:7]([C:9]2[N:10]=[N:11][C:12]([N:15]3[CH2:20][CH2:19][CH:18]([CH2:21][O:22][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[C:30]([F:33])([F:32])[F:31])[CH2:17][CH2:16]3)=[CH:13][CH:14]=2)=[O:8])[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 679582-TrifluoromethylphenolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 67171766HCID 67171766, compound

Product 1

HCID 11554163HCID 11554163, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 6-(4-hydroxymethylpiperidin-1-yl)pyridazine-3-carboxylic acid (2-cyclopropylethyl)amide (0.275 g, 0.90 mmol) in THF (10 mL) was added 2-hydroxybenzotrifluoride (0.178 g, 1.10 mmol), triphenylphosphine (0.289 g, 1.100 mmol) and diethyl azocarboxylate (0.5 mL, 1.10 mmol). The resulting mixture was stirred at ambient temperature for 18 hours. The solvent was removed in vacuo and the obtained crude product was purified by column chromatography to yield the title compound in 40% yield (0.035 g). 1H NMR (300 MHz, CDCl3) δ 7.98 (d, J=9.9 Hz, 2H), 7.54 (d, J=7.9 Hz, 1H), 7.47-7.42 (m, 1H), 6.99-6.92 (m, 3H), 4.57-4.53 (m, 2H), 3.89 (d, J=5.9 Hz, 2H), 3.56-3.49 (m, 2H), 3.11-3.02 (m, 2H), 2.25-2.15 (m, 1H), 2.01-1.97 (m, 2H), 1.52-1.41 (m, 2H), 1.27-1.20 (m, 2H), 0.75-0.68 (m, 1H), 0.47-0.41 (m, 2H), 0.09-0.05 (m, 2H). 13C NMR (75 MHz, CDCl3) δ 163.3, 160.0, 156.7, 144.3, 133.3, 127.2, 127.1, 126.8, 125.5, 120.1, 112.5, 112.2, 72.6, 44.9, 39.6, 36.1, 34.6, 28.2, 8.7, 4.2. MS (ES+) m/z 449 (M+1).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe obtained crude product
  3. customwas purified by column chromatography

Sources & evidence

ORD record
ord-79dc62bcea094713b043ae9489fb2326
Source dataset
uspto-grants-2011_05
Patent number
US07951805B2

Reaction notes

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