Diisopropylethylamine → HCID 178523262, compound

HRID 58784Notes

Reaction equation

HRID 58784 reaction equation
Cl.[NH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][CH2:12][NH2:13])=[N:3]1.[F:14][C:15]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:16]=1[CH2:17][C:18]1[O:22][N:21]=[C:20]([C:23](O)=[O:24])[CH:19]=1.C(N(CC)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.C(OCC)(=O)C>[NH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][CH2:12][NH:13][C:23]([C:20]2[CH:19]=[C:18]([CH2:17][C:16]3[CH:26]=[C:27]([F:30])[CH:28]=[CH:29][C:15]=3[F:14])[O:22][N:21]=2)=[O:24])=[N:3]1

Participants

7

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 178479205HCID 178479205, compound

Product 1

HCID 178523262HCID 178523262, compoundYield 9.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-(1H-indazol-3-yl)ethanamine hydrochloride (0.040 g; 0.202 mmol), 5-(2,5-difluorobenzyl)isoxazole-3-carboxylic acid (0.053 g; 0.223 mmol) N,N-diisopropylethylamine (0.87 mL; 0.506 mmol) and HATU (0.84 g; 0.223 mmol) in DMF (5 mL) was stirred at room temperature for 18 hours. The reaction mixture was diluted with ethyl acetate and washed with sodium hydrogen sulphate, sodium carbonate and brine. The organic layer was dried and concentrated under reduced pressure. The crude material was purified by flash chromatography on silica (eluent 1 to 10% methanol in dichloromethane) and by preparative HPLC method 4 to yield 0.007 g (9%) of the title compound as a white solid.

Workup

  1. washwashed with sodium hydrogen sulphate, sodium carbonate and brine
  2. customThe organic layer was dried
  3. concentrationconcentrated under reduced pressure
  4. customThe crude material was purified by flash chromatography on silica (eluent 1 to 10% methanol in dichloromethane) and by preparative HPLC method 4

Sources & evidence

ORD record
ord-dc16feaa611b4587a18ef7aebcc33011
Source dataset
uspto-grants-2016_09
Patent number
US09434722B2

Reaction notes

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