Diisopropylethylamine → HCID 86603085, compound

HRID 855394Notes

Reaction equation

HRID 855394 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:12]([OH:14])=O)[C:10]=1[F:11])[NH:7][CH:6]=[CH:5]2.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)C(C)C)(C)C.[CH:46]1([C:49]2[CH:68]=[CH:67][C:52]([CH2:53][NH:54][CH2:55][CH2:56][C:57]3[CH:62]=[CH:61][CH:60]=[C:59]([C:63]([F:66])([F:65])[F:64])[CH:58]=3)=[CH:51][CH:50]=2)[CH2:48][CH2:47]1>CN(C=O)C.O>[CH:46]1([C:49]2[CH:68]=[CH:67][C:52]([CH2:53][N:54]([CH2:55][CH2:56][C:57]3[CH:62]=[CH:61][CH:60]=[C:59]([C:63]([F:66])([F:65])[F:64])[CH:58]=3)[C:12]([C:9]3[C:10]([F:11])=[C:2]([Cl:1])[CH:3]=[C:4]4[C:8]=3[NH:7][CH:6]=[CH:5]4)=[O:14])=[CH:51][CH:50]=2)[CH2:48][CH2:47]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 251136475-chloro-6-fluoro-1H-indole-7-carboxylic acidHCID 68695622HCID 68695622, compound

Product 1

HCID 86603085HCID 86603085, compoundYield 49.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 37 mg (0.17 mmol) 5-chloro-6-fluoro-1H-indole-7-carboxylic acid and 54 mg of TBTU (0.17 mmol) in 2 ml DMF, were added 0.148 ml (0.87 mmol) of N,N-diisopropylethyl amine. After stirring for 5 min at rt, 51 mg (0.17 mmol) (4-cyclopropyl-benzyl)-[2-(3-trifluoromethyl-phenyl)-ethyl]-amine in 1 ml DMF was added. After stirring for 17 h at rt, the reaction mixture was diluted with 30 ml water and extracted with EtOAc (2×). The combined organic phases were washed with water and brine, dried with magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (8 g silica gel; diethylether/heptane 1:1; then 8 g silicagel DCM/heptane 70:30 to 90:10) to give 43 mg white foam (48%). MS (EI) 514.1 (M)+.

Workup

  1. stirringAfter stirring for 17 h at rt
  2. extractionextracted with EtOAc (2×)
  3. washThe combined organic phases were washed with water and brine
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (8 g silica gel

Sources & evidence

ORD record
ord-33c8978a17784a31977e777b73d212cc
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

Loading…