Diisopropylethylamine → HCID 71494103, compound

HRID 1750418Notes

Reaction equation

HRID 1750418 reaction equation
[CH:1]1([N:7]2[C:11]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)=[C:10]([C:19]3[S:20][CH:21]=[C:22]([CH2:24][C:25](O)=[O:26])[N:23]=3)[CH:9]=[N:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.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:61]1[CH2:66][CH2:65][CH:64]([CH2:67][NH2:68])[CH2:63][CH2:62]1>CN(C=O)C.O>[CH:1]1([N:7]2[C:11]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)=[C:10]([C:19]3[S:20][CH:21]=[C:22]([CH2:24][C:25]([NH:68][CH2:67][CH:64]4[CH2:65][CH2:66][O:61][CH2:62][CH2:63]4)=[O:26])[N:23]=3)[CH:9]=[N:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

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 86721262HCID 86721262, compound

Product 1

HCID 71494103HCID 71494103, compoundYield 71.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of the compound (50 mg, 0.13 mmol) obtained in step 4, HATU (74.0 mg, 0.19 mmol), DIEA (0.034 ml, 0.19 mmol) and (tetrahydro-2H-pyran-4-yl)methanamine (0.022 ml, 0.19 mmol) in DMF (2 mL) was stirred at room temperature for 2 days. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried, and the solvent was evaporated under reduced pressure. The obtained residue was crystallized from ethyl acetate and hexane to give the title compound (45 mg, 0.093 mmol, 71.9%) as a white powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was crystallized from ethyl acetate and hexane

Sources & evidence

ORD record
ord-7e7d9fb966724c4ca672037166d687ad
Source dataset
uspto-grants-2015_10
Patent number
US09156837B2

Reaction notes

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