Diisopropylethylamine → HCID 66832275, compound

HRID 58774Notes

Reaction equation

HRID 58774 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]2[C:11]([CH2:12][CH2:13][NH2:14])=[CH:10][NH:9][C:6]2=[N:7][CH:8]=1.F[C:16]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:17]=1[CH2:18][C:19]1ON=[C:21]([C:24](O)=O)[CH:20]=1.CN([C:35]([O:39]N1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH:56](N(CC)C(C)C)(C)[CH3:57]>CN(C=O)C>[Cl:2][C:3]1[CH:4]=[C:5]2[C:11]([CH2:12][CH2:13][NH:14][C:35](=[O:39])[C:24]3[CH:57]=[CH:56][C:19]([CH2:18][C:17]4[CH:16]=[CH:30][CH:29]=[C:28]([F:31])[CH:27]=4)=[CH:20][CH:21]=3)=[CH:10][NH:9][C:6]2=[N:7][CH:8]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 668320395-(2,5-Difluorobenzyl)isoxazole-3-carboxylic acidHCID 668320612-(5-chloro-1H-pyrrolo(2,3-b)pyridin-3-yl)ethan-1-amine hydrochloride

Product 1

HCID 66832275HCID 66832275, compoundYield 41.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The mixture of 2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)ethanamine hydrochloride (0.070 g; 0.301 mmol), 5-(2,5-difluorobenzyl)isoxazole-3-carboxylic acid (0.073 g; 0.304 mmol), HATU (N,N,N′,N′-Tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate) (0.116 g: 0.304 mmol) and N,N-diisopropylethylamine (0.132 mL; 0.754 mmol) in DMF (3 mL) was stirred for 72 hours at room temperature and was concentrated under reduced pressure. The residue was dissolved in dichloromethane and the organic layer was washed with water and concentrated under reduced pressure. The crude material was purified by flash chromatography on silica gel (eluent: 0 to 35% of ethyl acetate in dichloromethane) to give 0.051 g (40%) of N-(2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)ethyl)-4-(3-fluorobenzyl)benzamide as a white solid.

Workup

  1. concentrationwas concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in dichloromethane
  3. washthe organic layer was washed with water
  4. concentrationconcentrated under reduced pressure
  5. customThe crude material was purified by flash chromatography on silica gel (eluent: 0 to 35% of ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-9f36c21e214e4defa73dc2b57cfbc366
Source dataset
uspto-grants-2016_09
Patent number
US09434722B2

Reaction notes

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