Diisopropylethylamine → HCID 86721224, compound

HRID 1750382Notes

Reaction equation

HRID 1750382 reaction equation
[C:1]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[C:8]([C:18]2[N:19]=[C:20]([CH2:23][C:24]([OH:26])=O)[S:21][CH:22]=2)[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].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.[O:60]1[CH2:65][CH2:64][CH:63]([CH2:66][NH2:67])[CH2:62][CH2:61]1>CN(C=O)C.O>[C:1]([N:5]1[C:9]([C:10]2[CH:11]=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=2)=[C:8]([C:18]2[N:19]=[C:20]([CH2:23][C:24]([NH:67][CH2:66][CH:63]3[CH2:64][CH2:65][O:60][CH2:61][CH2:62]3)=[O:26])[S:21][CH:22]=2)[CH:7]=[N:6]1)([CH3:3])([CH3:4])[CH3:2]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 27732104-AminomethyltetrahydropyranHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86721223HCID 86721223, compound

Product 1

HCID 86721224HCID 86721224, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of the compound (54 mg, 0.15 mmol) obtained in step 7, HATU (66.3 mg, 0.17 mmol), DIEA (0.030 mL, 0.17 mmol) and (tetrahydro-2H-pyran-4-yl)methanamine (0.020 mL, 0.17 mmol) in DMF (2 mL) was stirred at room temperature for 3 days. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, aqueous sodium hydrogen carbonate solution and saturated brine and dried, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (solvent gradient; 80→100% ethyl acetate/hexane) to give the title compound (12 mg, 0.026 mmol, 18%)

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water, aqueous sodium hydrogen carbonate solution and saturated brine
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (solvent gradient; 80→100% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-6c7becab792d45519bb818dc36aecb5a
Source dataset
uspto-grants-2015_10
Patent number
US09156837B2

Reaction notes

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