HCID 11478544, compound → HCID 69384227, compound

HRID 916801Notes

Reaction equation

HRID 916801 reaction equation
[CH3:1][C:2]1([CH3:41])[O:7][C:6]2[CH:8]=[CH:9][C:10]([C@H:12]3[O:16]C(=O)[N:14]([CH2:18][CH2:19][C:20]4[CH:40]=[CH:39][C:23]([O:24][CH2:25][CH2:26][O:27][CH2:28][C:29]5[CH:30]=[C:31]([NH:35][C:36]([NH2:38])=[O:37])[CH:32]=[CH:33][CH:34]=5)=[CH:22][CH:21]=4)[CH2:13]3)=[CH:11][C:5]=2[CH2:4][O:3]1.CC1(C)OC2C=CC([C@H]3OC(=O)N(CCC4C=CC(OCCOCC5C=C(NC(=N)OC(=N)N)C=CC=5)=CC=4)C3)=CC=2CO1.O([Si](C)(C)C)[K]>C1COCC1>[CH3:1][C:2]1([CH3:41])[O:7][C:6]2[CH:8]=[CH:9][C:10]([C@@H:12]([OH:16])[CH2:13][NH:14][CH2:18][CH2:19][C:20]3[CH:21]=[CH:22][C:23]([O:24][CH2:25][CH2:26][O:27][CH2:28][C:29]4[CH:30]=[C:31]([NH:35][C:36]([NH2:38])=[O:37])[CH:32]=[CH:33][CH:34]=4)=[CH:39][CH:40]=3)=[CH:11][C:5]=2[CH2:4][O:3]1

Participants

5

Reactant 3

HCID 11478544HCID 11478544, compoundHCID 178431339HCID 178431339, compoundHCID 178504318HCID 178504318, compound

Product 1

HCID 69384227HCID 69384227, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

The mixture of N-(3-{[2-(4-{2-[(5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-3-yl]ethyl}phenoxy)ethoxy]methyl}phenyl)urea and N-(3-{[2-(4-{2-[(5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-3-yl]ethyl}phenoxy)ethoxy]methyl}phenyl)dicarbonimidic diamide (135 mg) in THF (2 mL) was treated with KOSiMe3 (123 mg) and the resulting solution was heated at 75° C. under nitrogen for 1.5 h. The reaction mixture was then quenched with MeOH and concentrated in vacuo. The residue was taken up in EtOAc, washed with water, dried (MgSO4) and concentrated in vacuo. The residue was purified by HPLC to give N-[3-({2-[4-(2-{[(2R)-2-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-hydroxyethyl]amino}ethyl)phenoxy]ethoxy}methyl)phenyl]urea (12 mg). LCMS RT=2.47 min and N-[3-([2-[4-(2-{[(2R)-2-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-hydroxyethyl]amino}ethyl)phenoxy]ethoxy}methyl)phenyl]dicarbonimidic diamide (6 mg). LCMS RT=2.58 min.

Workup

  1. customThe reaction mixture was then quenched with MeOH
  2. concentrationconcentrated in vacuo
  3. washwashed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-208d42b73de649a9823b160b11ec8242
Source dataset
uspto-grants-2007_09
Patent number
US07271197B2

Reaction notes

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