Dimethylformamide → HCID 49868910, compound

HRID 1777702Notes

Reaction equation

HRID 1777702 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:15][C:16]1[CH:17]=[C:18]([CH:29]=[CH:30]C=1)CC1C=CC(C(O)=O)=CC=1.CN(C([O:39][N:40]1N=N[C:42]2[CH:43]=[CH:44][CH:45]=N[C:41]1=2)=[N+](C)C)C.[F:49][P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.CN([CH:68]=[O:69])C>>[Cl:2][C:3]1[CH:4]=[C:5]2[C:11]([CH2:12][CH2:13][NH:14][C:68]([C:41]3[CH:42]=[C:43]([CH2:44][C:45]4[CH:30]=[C:29]([F:49])[CH:18]=[CH:17][C:16]=4[F:15])[O:39][N:40]=3)=[O:69])=[CH:10][NH:9][C:6]2=[N:7][CH:8]=1

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 668320612-(5-chloro-1H-pyrrolo(2,3-b)pyridin-3-yl)ethan-1-amine hydrochlorideHCID 679746154-(3-Fluoro-benzyl)-benzoic acid

Product 1

HCID 49868910HCID 49868910, compoundYield 49%

Procedure

A mixture of 2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)ethanamine hydrochloride (0.070 g; 0.301 mmol), 4-(3-fluorobenzyl)benzoic acid (0.0701 g; 0.304 mmol), HATU (0.116 g: 0.304 mmol) and N,N-diisopropylethylamine (0.132 mL; 0.754 mmol) in DMF (3 mL) was stirred during the weekend at room temperature and was concentrated in vacuo. 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 0.061 g (49%) of N-(2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)ethyl)-5-(2,5-difluorobenzyl)isoxazole-3-carboxamide as a white solid.

Workup

  1. concentrationwas concentrated in vacuo
  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-d555625847f4416a8f5a0385ff0e2853
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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