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Diisopropylethylamine → HCID 86721284, compound

HRID 1750441
Notes
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Reaction equation

HRID 1750441 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](/[CH:23]=[CH:24]/[C:25](O)=[O:26])[N:22]=2)[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[NH2:28][CH2:29][CH:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>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[S:19][CH:20]=[C:21](/[CH:23]=[CH:24]/[C:25]([NH:28][CH2:29][CH:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)=[O:26])[N:22]=2)[CH:7]=[N:6]1)([CH3:2])([CH3:4])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 86721282HCID 86721282, compound

Product 1

HCID 86721284HCID 86721284, compoundYield 47.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of the compound (90 mg, 0.23 mmol) obtained in step 5, 4-(aminomethyl)tetrahydropyran (0.029 mL, 0.26 mmol), DIEA (0.049 mL, 0.28 mmol) and HATU (107 mg, 0.28 mmol) in DMF (2.0 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 water and saturated brine and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by NH-silica gel column chromatography (solvent gradient; 50→80% ethyl acetate/hexane) and crystallized from ethyl acetate and hexane to give the title compound (52.7 mg, 0.110 mmol, 46.7%) 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 purified by NH-silica gel column chromatography (solvent gradient; 50→80% ethyl acetate/hexane)
  6. customcrystallized from ethyl acetate and hexane

Sources & evidence

ORD record
ord-7b667c81a7fd4405b0bd10ddd279493c
Source dataset
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09156837B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes