Tributylamine → methyl 2-acetylamino-3-[2-[(2S)-2-(benzenesulfonylamino)-3-[4-(4-piperidyloxy)phenyl]propoxy]-4-cyanophenyl]acrylate

HRID 747765Notes

Reaction equation

HRID 747765 reaction equation
[C:1]1([S:7]([NH:10][C@@H:11]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH:31]3[CH2:36][CH2:35][N:34](C(OCC4C=CC=CC=4)=O)[CH2:33][CH2:32]3)=[CH:26][CH:25]=2)[CH2:12][O:13][C:14]2[CH:15]=[C:16]([CH:19]=[CH:20][C:21]=2I)[C:17]#[N:18])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:47]([C:51](=[CH2:56])[C:52]([O:54][CH3:55])=[O:53])[C:48]([CH3:50])=[O:49].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CCCC)CCCC)CCC>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:48]([NH:47][C:51](=[CH:56][C:21]1[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][C:14]=1[O:13][CH2:12][C@@H:11]([NH:10][S:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)(=[O:9])=[O:8])[CH2:23][C:24]1[CH:25]=[CH:26][C:27]([O:30][CH:31]2[CH2:32][CH2:33][NH:34][CH2:35][CH2:36]2)=[CH:28][CH:29]=1)[C:52]([O:54][CH3:55])=[O:53])(=[O:49])[CH3:50]

Participants

7

Reactant 4

HCID 7622TributylamineHCID 80271Tri-o-tolylphosphineHCID 98644Methyl 2-acetamidoacrylateHCID 688344743-[(2S)-2-(benzenesulfonylamino)-3-[4-(1-benzyloxycarbonyl-4-piperidyloxy)phenyl]propoxy]-4-iodobenzonitrile

Product 1

HCID 68830749methyl 2-acetylamino-3-[2-[(2S)-2-(benzenesulfonylamino)-3-[4-(4-piperidyloxy)phenyl]propoxy]-4-cyanophenyl]acrylate

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

197 mg (0.26 mmol)) of 3-[(2S)-2-(benzenesulfonylamino)-3-[4-(1-benzyloxycarbonyl-4-piperidyloxy)phenyl]propoxy]-4-iodobenzonitrile and 74.4 mg (0.52 mmol) of methyl 2-acetaminoacrylate were dissolved in 6 ml of acetonitrile. 7.3 mg (0.03 mmol) of palladium (II) acetate, 55 mg (0.18 mmol) of tri-o-tolylphosphine and 96 mg (0.52 mmol) of tributylamine were added to the solution, and they were heated under reflux overnight. The solvent was distilled off and the residue was treated with ethyl acetate as the extractant in an ordinary manner to obtain the crude product, which was purified by the silica gel column chromatography to obtain the title compound.

Workup

  1. temperaturewere heated
  2. temperatureunder reflux overnight
  3. distillationThe solvent was distilled off
  4. additionthe residue was treated with ethyl acetate as the extractant in an ordinary manner
  5. customto obtain the crude product, which
  6. customwas purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-c8021bf472444a10bad9b2391e7c4e9e
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

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