Diisopropylethylamine → HCID 68592522, compound

HRID 1429147Notes

Reaction equation

HRID 1429147 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([NH:11][C:12]([CH:14]2[CH2:18][CH:17]([O:19][C:20]3[CH:25]=[C:24]([O:26][CH3:27])[N:23]=[C:22]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[N:21]=3)[CH2:16][CH:15]2[C:34](O)=[O:35])=[O:13])[CH2:8][CH:7]1[CH:9]=[CH2:10])=[O:5])[CH3:2].CCN(C(C)C)C(C)C.Cl.[CH3:47][NH:48][CH:49]=[CH:50][CH2:51][CH2:52][CH2:53][CH3:54].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1([NH:11][C:12]([CH:14]2[CH2:18][CH:17]([O:19][C:20]3[CH:25]=[C:24]([O:26][CH3:27])[N:23]=[C:22]([C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)[N:21]=3)[CH2:16][CH:15]2[C:34](=[O:35])[N:48]([CH2:49][CH2:50][CH2:51][CH2:52][CH:53]=[CH2:54])[CH3:47])=[O:13])[CH2:8][CH:7]1[CH:9]=[CH2:10])=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68592566HCID 68592566, compoundHCID 86641379HCID 86641379, compound

Product 1

HCID 68592522HCID 68592522, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound 7b (1.32 g, 2.67 mmol) was dissolved in 30 ml dry DMF. DIEA (2.1 ml, 12.0 mmol), N-methylhexeneamine HCl (440 mg, 3.9 mmol) and HATU (1.48 g, 3.9 mmol) were added at 0° C., and the reaction mixture was stirred at RT over night. The DMF was evaporated and the residue was dissolved in EtOAc, washed with sat. NaHCO3(aq), H2O and brine. The organic layer was dried (MgSO4), filtered and evaporated, followed by column chromatography (Heptane/EtOAc), giving the title compound. (1.1 g, 70%), MS (M+H)+591.

Workup

  1. customThe DMF was evaporated
  2. dissolutionthe residue was dissolved in EtOAc
  3. washwashed with sat. NaHCO3(aq), H2O and brine
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-088e24e0cb294c4bb9dbb6beadb433d3
Source dataset
uspto-grants-2015_01
Patent number
US08937080B2

Reaction notes

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