Diisopropylethylamine → HCID 71496744, compound

HRID 1750405Notes

Reaction equation

HRID 1750405 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[S:19][CH:20]=[C:21]([CH2:23][C:24]([OH:26])=O)[N: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:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[C:8]([C:18]2[S:19][CH:20]=[C:21]([CH2:23][C:24]([NH:67][CH2:66][CH:63]3[CH2:64][CH2:65][O:60][CH2:61][CH2:62]3)=[O:26])[N: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 86721248HCID 86721248, compound

Product 1

HCID 71496744HCID 71496744, compoundYield 93.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of the compound (780 mg, 2.10 mmol) obtained in step 13, HATU (958 mg, 2.52 mmol), DIEA (0.439 ml, 2.52 mmol) and (tetrahydro-2H-pyran-4-yl)methanamine (290 mg, 2.52 mmol) in DMF (10 mL) was stirred at room temperature for 14 hr. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine and dried, and the solvent was evaporated under reduced pressure to give the title compound (918 mg, 1.959 mmol, 93%) as a white powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine
  3. customdried
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-f4571591bcfb4841a4193c5d2f76d0e9
Source dataset
uspto-grants-2015_10
Patent number
US09156837B2

Reaction notes

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