Tributyl(5-fluorobenzofuran-2-yl)stannane → 2-{2-[5-(5-Fluorobenzofuran-2-yl)pyridin-3-yl]-6-propylpyrimidin-4-ylamino}-4-methylpentanoic acid (3-ethoxypropyl) amide

HRID 1822797Notes

Reaction equation

HRID 1822797 reaction equation
C([Sn](CCCC)(CCCC)[C:6]1[O:7][C:8]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:9]=2[CH:10]=1)CCC.[CH2:24]([O:26][CH2:27][CH2:28][CH2:29][NH:30][C:31](=[O:55])[CH:32]([NH:37][C:38]1[CH:43]=[C:42]([CH2:44][CH2:45][CH2:46]C)[N:41]=[C:40]([C:48]2[CH:49]=[N:50][CH:51]=[C:52](Br)[CH:53]=2)[N:39]=1)[CH2:33][CH:34]([CH3:36])[CH3:35])[CH3:25]>CN(C)C=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:24]([O:26][CH2:27][CH2:28][CH2:29][NH:30][C:31](=[O:55])[CH:32]([NH:37][C:38]1[CH:43]=[C:42]([CH2:44][CH2:45][CH3:46])[N:41]=[C:40]([C:48]2[CH:49]=[N:50][CH:51]=[C:52]([C:6]3[O:7][C:8]4[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:9]=4[CH:10]=3)[CH:53]=2)[N:39]=1)[CH2:33][CH:34]([CH3:35])[CH3:36])[CH3:25]

Participants

5

Reactant 2

HCID 22170021Tributyl(5-fluorobenzofuran-2-yl)stannaneHCID 865921672-[2-(5-Bromopyridin-3-yl)-6-butylpyrimidin-4-ylamino]-4-methylpentanoic acid (3-ethoxypropyl)amide

Product 1

HCID 235687132-{2-[5-(5-Fluorobenzofuran-2-yl)pyridin-3-yl]-6-propylpyrimidin-4-ylamino}-4-methylpentanoic acid (3-ethoxypropyl) amideYield 21.3%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

Under an atmosphere of argon, a solution of tributyl(5-fluorobenzofuran-2-yl)stannane (17 mg), 2-[2-(5-bromopyridin-3-yl)-6-butylpyrimidin-4-ylamino]-4-methylpentanoic acid (3-ethoxypropyl)amide (20 mg) and (PPh3)2PdCl2 (2 mg) in N,N-dimethylformamide (1 mL) was heated at 80° C. for 12 h and then quenched with water (10 mL). The mixture was extracted with ethyl acetate (3×20 mL) and the combined organic extracts were dried over sodium sulfate and concentrated. The crude product was purified by semi-preparative HPLC to give 4.6 mg of 2-{2-[5-(5-fluorobenzofuran-2-yl)pyridin-3-yl]-6-propylpyrimidin-4-ylamino}-4-methylpentanoic acid (3-ethoxypropyl) amide as a TFA salt. ESI-MS (m/z) 562 [M+H]+.

Workup

  1. customquenched with water (10 mL)
  2. extractionThe mixture was extracted with ethyl acetate (3×20 mL)
  3. dry with materialthe combined organic extracts were dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe crude product was purified by semi-preparative HPLC

Sources & evidence

ORD record
ord-10c23bc8ca3e452a98d90497f790f6e1
Source dataset
uspto-grants-2006_05
Patent number
US07037916B2

Reaction notes

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