Diisopropylethylamine → HCID 86650417, compound

HRID 240118Notes

Reaction equation

HRID 240118 reaction equation
CCN(C(C)C)C(C)C.[F:10][C:11]([F:28])([F:27])[O:12][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[O:21][C:20](=[O:23])[C:19]([C:24]([OH:26])=O)=[CH:18]2.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH:53]1[C:61]2[C:56](=[CH:57][C:58]([C:62]3[CH:63]=[C:64]([NH2:68])[CH:65]=[CH:66][CH:67]=3)=[CH:59][CH:60]=2)[CH:55]=[CH:54]1>CN(C=O)C>[NH:53]1[C:61]2[C:56](=[CH:57][C:58]([C:62]3[CH:63]=[C:64]([NH:68][C:24]([C:19]4[C:20](=[O:23])[O:21][C:22]5[C:17]([CH:18]=4)=[CH:16][CH:15]=[CH:14][C:13]=5[O:12][C:11]([F:10])([F:28])[F:27])=[O:26])[CH:65]=[CH:66][CH:67]=3)=[CH:59][CH:60]=2)[CH:55]=[CH:54]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 4135989HCID 4135989, compoundHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 866503588-Trifluoromethoxy-3-carboxy-coumarin

Product 1

HCID 86650417HCID 86650417, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

DIEA (0.014 mL, 0.073 mmol) was added to 8-trifluoromethoxy-3-carboxy-coumarin (0.020 g, 0.066 mmol) and HATU (0.030 g, 0.073 mmol) in 0.36 mL of DMF with constant stirring at room temperature until a clear solution resulted. Subsequently, 3-(1H-Indol-5-yl)-phenylamine (0.015 g, 0.066 mmol) was added and allowed to react overnight. DMF was removed under vacuum and the reaction was resuspended in DMSO. The crude product was purified on a Parallex Flex parallel preparative reverse phase HPLC instrument (Biotage) using a solvent gradient of 10-95% ACN/H2O with 0.05% TFA at a flow rate of 20 mL/min. UV absorbance was monitored at 254 nm and the fractions corresponding to the product peak were collected were collected and the solvent removed under vacuum to give 0.023 g of product in 68% yield: LCMS (ESI) m/z 465 (MH+).

Workup

  1. customresulted
  2. customto react overnight
  3. customDMF was removed under vacuum
  4. customThe crude product was purified on a Parallex Flex parallel preparative reverse phase HPLC instrument (Biotage)
  5. customthe fractions corresponding to the product peak were collected
  6. customwere collected
  7. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-55650da75f744fafbd68f3ce0f07d5f1
Source dataset
uspto-grants-2014_02
Patent number
US08642788B2

Reaction notes

Loading…