Diisopropylethylamine → HCID 68467482, compound

HRID 507226Notes

Reaction equation

HRID 507226 reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)C(C)C)C.[CH:32]1([CH2:35][C:36]([OH:38])=O)[CH2:34][CH2:33]1.[Cl:39][C:40]1[CH:70]=[CH:69][C:43]([CH2:44][N:45]2[C:49]3[CH:50]=[C:51]([N:55]4[CH2:60][CH2:59][NH:58][CH2:57][CH2:56]4)[C:52]([F:54])=[CH:53][C:48]=3[N:47]=[C:46]2[CH2:61][O:62][C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=2)=[CH:42][CH:41]=1>CN(C=O)C.O>[Cl:39][C:40]1[CH:70]=[CH:69][C:43]([CH2:44][N:45]2[C:49]3[CH:50]=[C:51]([N:55]4[CH2:60][CH2:59][N:58]([C:36](=[O:38])[CH2:35][CH:32]5[CH2:33][CH2:34]5)[CH2:57][CH2:56]4)[C:52]([F:54])=[CH:53][C:48]=3[N:47]=[C:46]2[CH2:61][O:62][C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=2)=[CH:42][CH:41]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 138440Cyclopropaneacetic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 68467472HCID 68467472, compound

Product 1

HCID 68467482HCID 68467482, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

71 mg of TBTU (0.22 mmol), 0.19 ml of ethyldiisopropylamine and 0.022 ml of cyclopropyl-acetic acid were dissolved in 6 ml DMF and stirred for one minute at rt under argon. Then 100 mg of 1-(4-chloro-benzyl)-5-fluoro-2-phenoxymethyl-6-piperazin-1-yl-1H-benzoimidazole (0.22 mmol) were added and the reaction mixture was stirred for 22 h at rt. The reaction mixture was then diluted with 30 ml water and extracted with ethylacetate (twice). The combined organic phases were washed with water and brine, dried with magnesium sulfate, filtered and concentrated in vacuo, leading to 130 mg of a light red solid (100%). MS (ISP) 533.4 (M+H)+.

Workup

  1. stirringthe reaction mixture was stirred for 22 h at rt
  2. extractionextracted with ethylacetate (twice)
  3. washThe combined organic phases were washed with water and brine
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-14c4f37fe42342cdbdec190a579dc36f
Source dataset
uspto-grants-2010_08
Patent number
US07786128B2

Reaction notes

Loading…