Hydrochloric Acid → HCID 68590569, compound

HRID 1429134Notes

Reaction equation

HRID 1429134 reaction equation
[C:1]([C:5]1[N:10]=[C:9]([O:11][CH3:12])[N:8]=[C:7]([O:13][CH:14]2[CH2:18][CH:17]([C:19](O)=[O:20])[CH:16]([C:22](=[O:34])[NH:23][C:24]3([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:26][CH:25]3[CH:27]=[CH2:28])[CH2:15]2)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.[CH3:44][NH:45][CH:46]=[CH:47][CH2:48][CH2:49][CH2:50][CH3:51].Cl.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH2:32]([O:31][C:29]([C:24]1([NH:23][C:22]([CH:16]2[CH2:15][CH:14]([O:13][C:7]3[CH:6]=[C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[N:10]=[C:9]([O:11][CH3:12])[N:8]=3)[CH2:18][CH:17]2[C:19](=[O:20])[N:45]([CH2:46][CH2:47][CH2:48][CH2:49][CH:50]=[CH2:51])[CH3:44])=[O:34])[CH2:26][CH:25]1[CH:27]=[CH2:28])=[O:30])[CH3:33]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68590160HCID 68590160, compoundHCID 86641378HCID 86641378, compound

Product 1

HCID 68590569HCID 68590569, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound 3g (583 mg, 1.227 mmol) was dissolved in 15 ml dry DMF. DIEA (0.96 ml, 5.522 mmol), N-methylhexeneamine×HCl (270 mg, 1.779 mmol) and HATU (676 mg, 1.779 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 and washed with saturated NaHCO3(aq), H2O and brine. The organic layer was dried (MgSO4), filtered and evaporated. Purification by column chromatography (heptane/EtOAc) gave the pure title compound (550 mg, 78%), MS (M+H)+573.

Workup

  1. customThe DMF was evaporated
  2. dissolutionthe residue was dissolved in EtOAc
  3. washwashed with saturated NaHCO3(aq), H2O and brine
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customPurification by column chromatography (heptane/EtOAc)

Sources & evidence

ORD record
ord-1c4e35f584dd4f4ab0717d05c6608199
Source dataset
uspto-grants-2015_01
Patent number
US08937080B2

Reaction notes

Loading…