Diisopropylethylamine → HCID 11606213, compound

HRID 855391Notes

Reaction equation

HRID 855391 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.[C:46]([C:50]1[CH:69]=[CH:68][C:53]([CH2:54][NH:55][CH2:56][CH2:57][C:58]2[CH:63]=[CH:62][CH:61]=[C:60]([C:64]([F:67])([F:66])[F:65])[CH:59]=2)=[CH:52][CH:51]=1)([CH3:49])([CH3:48])[CH3:47]>CN(C=O)C.O>[C:46]([C:50]1[CH:69]=[CH:68][C:53]([CH2:54][N:55]([CH2:56][CH2:57][C:58]2[CH:63]=[CH:62][CH:61]=[C:60]([C:64]([F:67])([F:65])[F:66])[CH:59]=2)[C:12]([C:9]2[C:10]([F:11])=[C:2]([Cl:1])[CH:3]=[C:4]3[C:8]=2[NH:7][CH:6]=[CH:5]3)=[O:14])=[CH:52][CH:51]=1)([CH3:49])([CH3:47])[CH3:48]

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 68560440(4-Tert-butyl-benzyl)-[2-(3-trifluoromethyl-phenyl)-ethyl]-amine

Product 1

HCID 11606213HCID 11606213, compoundYield 27.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 185 mg (0.87 mmol) 5-chloro-6-fluoro-1H-indole-7-carboxylic acid and 278 mg of TBTU (0.87 mmol) in 13 ml DMF, were added 0.74 ml (4.33 mmol) of N,N-diisopropylethyl amine. After stirring for 5 min at rt, 290 mg (0.87 mmol) (4-tert-butyl-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 140 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 two successive column chromatographies (90 g silica gel; diethylether/heptane 1:1; then 8 g silica gel; DCM/heptane 70:30 to 90:10) to give 125 mg white foam (27%). M (EI) 530.2 (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 two successive column chromatographies (90 g silica gel

Sources & evidence

ORD record
ord-c03bd859874b475993a8cca79e32f330
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

Loading…