Diisopropylethylamine → HCID 178496869, compound

HRID 1183812Notes

Reaction equation

HRID 1183812 reaction equation
NCCNC(=O)OCC1C=CC=CC=1.[N:15]([C:18](=[CH:23][C:24]1[CH:32]=[CH:31][CH:30]=[C:29]2[C:25]=1[CH:26]=[CH:27][NH:28]2)[C:19]([O:21][CH3:22])=[O:20])=[N+]=[N-].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[CH:23]1[C:24]2=[C:25]3[C:29]([CH:30]=[CH:31][C:32]2=[N:15][C:18]=1[C:19]([O:21][CH3:22])=[O:20])=[N:28][CH:27]=[CH:26]3

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2794257Benzyl N-(2-aminoethyl)carbamateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 72253810methyl 2-azido-3-(1H-indol-4-yl)acrylate

Product 1

HCID 178496869HCID 178496869, compoundYield 260.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To compound 1 (50 mg, 0.079 mmol) in DMF (2 mL) was added 2 (49 mg, 0.085 mmol) and HATU (33 mg, 0.086 mmol) followed by adding DIPEA (45 uL) and the reaction mixture was stirred for 4 hrs at room temperature. The solvent was removed under vacuo and the product was purified by Prep HPLC (SymmetrPrep C18, 7 μm, 19×150 mm column), eluted at 10 ml/min (0.01% TFA in water/acetonitrile) with a gradient: 10% acetonitrile in 5 min, 10% to 50% acetonitrile in 15 min, maintaining 50% acetonitrile in 5 min, 50% to 100% acetonitrile in 5 min, to give 3 (47 mg, 60%). MS: (M+H)+ 1003.

Workup

  1. customThe solvent was removed under vacuo
  2. customthe product was purified by Prep HPLC (SymmetrPrep C18, 7 μm, 19×150 mm column)
  3. washeluted at 10 ml/min (0.01% TFA in water/acetonitrile) with a gradient
  4. wait10% acetonitrile in 5 min
  5. wait10% to 50% acetonitrile in 15 min
  6. temperaturemaintaining 50% acetonitrile in 5 min
  7. wait50% to 100% acetonitrile in 5 min

Sources & evidence

ORD record
ord-ac5a7ece997846e7be5c5b1f9bbf7d24
Source dataset
uspto-grants-2014_03
Patent number
US08664407B2

Reaction notes

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