Triphenylphosphine → N-cyclopropyl-4-methyl-3-{[4-(1-pyridin-2-ylethoxy)benzoyl]amino}benzamide

HRID 403046Notes

Reaction equation

HRID 403046 reaction equation
[OH:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([NH:8][C:9]2[CH:10]=[C:11]([CH:18]=[CH:19][C:20]=2[CH3:21])[C:12]([NH:14][CH:15]2[CH2:17][CH2:16]2)=[O:13])=[O:7])=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:43]1[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=1[CH:49](O)[CH3:50].N(C(OCC)=O)=NC(OCC)=O>C(Cl)Cl>[CH:15]1([NH:14][C:12](=[O:13])[C:11]2[CH:18]=[CH:19][C:20]([CH3:21])=[C:9]([NH:8][C:6](=[O:7])[C:5]3[CH:4]=[CH:3][C:2]([O:1][CH:49]([C:44]4[CH:45]=[CH:46][CH:47]=[CH:48][N:43]=4)[CH3:50])=[CH:23][CH:22]=3)[CH:10]=2)[CH2:16][CH2:17]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 86784alpha-Methyl-2-pyridinemethanolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 66631169N-cyclopropyl-3-[(4-hydroxybenzoyl)amino]-4-methylbenzamide

Product 1

HCID 11464157N-cyclopropyl-4-methyl-3-{[4-(1-pyridin-2-ylethoxy)benzoyl]amino}benzamideYield 14.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 3-{[4-(hydroxy)benzoyl]amino}-N-cyclopropyl-4-methylbenzamide (150 mg, 0.484 mmol) in DCM (20 mL) was added polymer supported triphenyl phosphine (937 mg, 1.45 mmol) and the 1-pyridin-2-ylethanol (45 mg, 0.363 mmol). Diethyl azodicarboxylate (126 mg, 0.726 mmol) was then added dropwise. The reaction was stirred for 17 h at room temperature and was then filtered and the filtrates were evaporated. The crude residue was purified by flash silica chromatography using ethyl acetate in iso-hexane (5-100%) as the eluent to give the title compound as a colourless oil (22 mg, 11%); NMR Spectrum: (DMSOd6) 0.55 (m, 2H), 0.68 (m, 2H), 1.64 (d, 3H), 2.22 (s, 3H), 2.83 (m, 1H), 5.60 (q, 1H), 7.02 (d, 2H), 7.31 (d, 2H), 7.43 (d, 1H), 7.62 (d, 1H), 7.80 (m, 2H), 7.90 (d, 2H), 8.35 (d, 1H), 8.58 (d, 1H), 9.75 (s, 1H); Mass Spectrum: M+H+ 416.

Workup

  1. filtrationwas then filtered
  2. customthe filtrates were evaporated
  3. customThe crude residue was purified by flash silica chromatography

Sources & evidence

ORD record
ord-adce1b132f5446c289823d8f4bf6850a
Source dataset
uspto-grants-2014_06
Patent number
US08742124B2

Reaction notes

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