Imidazole → HCID 11189641, compound

HRID 1026679Notes

Reaction equation

HRID 1026679 reaction equation
[O:1]1[C:3]2([CH2:8][CH2:7][N:6]([C:9]3[CH:14]=[CH:13][C:12]([N:15]4[CH2:19][C@H:18]([CH2:20][NH:21][C:22](=[O:24])[CH3:23])[O:17][C:16]4=[O:25])=[CH:11][C:10]=3[F:26])[CH2:5][CH2:4]2)[CH2:2]1.B(F)(F)F.[NH:31]1[CH:35]=[CH:34][N:33]=[CH:32]1>CN(C)C=O>[NH:31]1[CH:35]=[CH:34][N:33]=[C:32]1[CH2:2][C:3]1([OH:1])[CH2:4][CH2:5][N:6]([C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:19][C@H:18]([CH2:20][NH:21][C:22](=[O:24])[CH3:23])[O:17][C:16]3=[O:25])=[CH:11][C:10]=2[F:26])[CH2:7][CH2:8]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 6356Boron trifluorideHCID 11382912HCID 11382912, compound

Product 1

HCID 11189641HCID 11189641, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound was obtained by reacting (S)—N-{3-[4-(1-oxa-6-aza-spiro[2.5]oct-6-yl)-3-fluorophenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide (1.40 mmol), BF3 etherate (catalytic) and imidazole (1.80 mmol) in dimethylformamide (10 ml) at 80° C. for 8 hours, followed by silica gel column chromatographic separation to provide title compound in 66% yield. M.P. 130-132° C. and MS (M+1)=432 (MH+, 100%) for M.F.=C21H26FN5O4.

Workup

  1. customThe compound was obtained
  2. customat 80° C.
  3. customfor 8 hours
  4. customfollowed by silica gel column chromatographic separation

Sources & evidence

ORD record
ord-ae24d99d48954aeaa2f15019b5871f13
Source dataset
uspto-grants-2014_05
Patent number
US08729269B2

Reaction notes

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