Diisopropylethylamine → HCID 86721244, compound

HRID 1750400Notes

Reaction equation

HRID 1750400 reaction equation
[Br:1][C:2]1[N:6]([C:7]([CH3:10])([CH3:9])[CH3:8])[N:5]=[CH:4][C:3]=1[C:11]1[S:12][CH:13]=[C:14]([CH2:16][C:17]([OH:19])=O)[N:15]=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:53]1[CH2:58][CH2:57][CH:56]([CH2:59][NH2:60])[CH2:55][CH2:54]1>CN(C=O)C.O>[Br:1][C:2]1[N:6]([C:7]([CH3:8])([CH3:9])[CH3:10])[N:5]=[CH:4][C:3]=1[C:11]1[S:12][CH:13]=[C:14]([CH2:16][C:17]([NH:60][CH2:59][CH:56]2[CH2:57][CH2:58][O:53][CH2:54][CH2:55]2)=[O:19])[N:15]=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 86721243HCID 86721243, compound

Product 1

HCID 86721244HCID 86721244, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of the compound (1.8 g, 5.23 mmol) obtained in step 7, HATU (2.386 g, 6.27 mmol), DIEA (1.093 mL, 6.27 mmol) and (tetrahydro-2H-pyran-4-yl)methanamine (0.723 g, 6.27 mmol) in DMF (1 mL) was stirred at room temperature for 2 hr. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 50% ethyl acetate/hexane→5% methanol/ethyl acetate) to give 2-(2-(5-bromo-1-tert-butyl-1H-pyrazol-4-yl)thiazol-4-yl)-N-((tetrahydro-2H-pyran-4-yl)methyl)acetamide (2.31 g, 5.23 mmol, 100%) as a colorless oil

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 50% ethyl acetate/hexane→5% methanol/ethyl acetate)

Sources & evidence

ORD record
ord-9d280dedcece458d996f4486cc15bce2
Source dataset
uspto-grants-2015_10
Patent number
US09156837B2

Reaction notes

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