1-Methyl-2-(tributylstannyl)-1H-imidazole → N-((1S)-1-((1R)-2-(((4'S)-6'-(2,2-dimethylpropyl)-8'-(1-methyl-1H-imidazol-2-yl)-3',4'-dihydrospiro[cyclobutane-1,2'-pyrano[2,3-c]pyridin]-4'-yl)amino)-1-hydroxyethyl)-3-buten-1-yl)-2-methoxyacetamide

HRID 473387Notes

Reaction equation

HRID 473387 reaction equation
Cl[C:2]1[N:3]=[C:4]([CH2:29][C:30]([CH3:33])([CH3:32])[CH3:31])[CH:5]=[C:6]2[C@@H:11]([NH:12][CH2:13][C@H:14]([C@@H:16]([NH:20][C:21](=[O:25])[CH2:22][O:23][CH3:24])[CH2:17][CH:18]=[CH2:19])[OH:15])[CH2:10][C:9]3([CH2:28][CH2:27][CH2:26]3)[O:8][C:7]=12.[CH3:34][N:35]1[CH:39]=[CH:38][N:37]=[C:36]1[Sn](CCCC)(CCCC)CCCC>C1COCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:32][C:30]([CH3:31])([CH3:33])[CH2:29][C:4]1[CH:5]=[C:6]2[C@@H:11]([NH:12][CH2:13][C@H:14]([C@@H:16]([NH:20][C:21](=[O:25])[CH2:22][O:23][CH3:24])[CH2:17][CH:18]=[CH2:19])[OH:15])[CH2:10][C:9]3([CH2:28][CH2:27][CH2:26]3)[O:8][C:7]2=[C:2]([C:36]2[N:35]([CH3:34])[CH:39]=[CH:38][N:37]=2)[N:3]=1

Participants

6

Reactant 2

HCID 27632521-Methyl-2-(tributylstannyl)-1H-imidazoleHCID 86678557HCID 86678557, compound

Product 1

HCID 57515884N-((1S)-1-((1R)-2-(((4'S)-6'-(2,2-dimethylpropyl)-8'-(1-methyl-1H-imidazol-2-yl)-3',4'-dihydrospiro[cyclobutane-1,2'-pyrano[2,3-c]pyridin]-4'-yl)amino)-1-hydroxyethyl)-3-buten-1-yl)-2-methoxyacetamide

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
160 °C

Procedure

A solution of N-((1S)-1-((1R)-2-(((4′S)-8′-chloro-6′-(2,2-dimethylpropyl)-3′,4′-dihydrospiro[cyclobutane-1,2′-pyrano[2,3-c]pyridin]-4′-yl)amino)-1-hydroxyethyl)-3-buten-1-yl)-2-methoxyacetamide (225 mg, 469 μmol) and tetrakis(triphenylphosphine)palladium (108 mg, 93.7 μmol) in THF (3.0 mL) is added to a vial with 1-methyl-2-(tributylstannyl)-1H-imidazole (217 mg, 586 μmol). The reaction was heated in the microwave at 160° C. for 20 min. The residue was diluted with H2O (10 mL) and extracted with CH2Cl2 (3×10 ml). The organic layers were dried (MgSO4), concentrated and purified by reverse phase HPLC to give the title compound as a white amorphous solid. MS m/z=526.3 [M+H]+.

Workup

  1. extractionextracted with CH2Cl2 (3×10 ml)
  2. dry with materialThe organic layers were dried (MgSO4)
  3. concentrationconcentrated
  4. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-e358a24009e74818884014f0cd3a16a0
Source dataset
uspto-grants-2014_01
Patent number
US08633315B2

Reaction notes

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