2-(4-Chlorophenyl)ethylamine → HCID 68512002, compound

HRID 1810109Notes

Reaction equation

HRID 1810109 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([OH:12])=O)=[CH:7][CH:8]=2)[CH:3]=[N:2]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[Cl:46][C:47]1[CH:52]=[CH:51][C:50]([CH2:53][CH2:54][NH2:55])=[CH:49][CH:48]=1>CN(C=O)C.O>[Cl:46][C:47]1[CH:52]=[CH:51][C:50]([CH2:53][CH2:54][NH:55][C:10]([C:6]2[CH:5]=[C:4]3[C:9](=[CH:8][CH:7]=2)[NH:1][N:2]=[CH:3]3)=[O:12])=[CH:49][CH:48]=1

Participants

7

Reactant 4

HCID 674302-(4-Chlorophenyl)ethylamineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 42484541H-Indazole-5-carboxylic acid

Product 1

HCID 68512002HCID 68512002, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of the 1H-indazole-5carboxylic acid (215 mg, 1.32 mmol) and HBTU (553 mg, 1.45 mmol) in DMF (5 mL) was added DIEA (277 μL, 1.59 mmol) followed by 2-(4chlorophenyl)ethylamine (222 μL, 1.59 mmol). The reaction was stirred overnight, then diluted with water and extracted with EtOAc. The combined organic layers were washed with brine and dried over MgSO4. The crude product was purified over silica gel on a Biotage Horizon high-performance flash chromatography system (25+M silica gel cartridge) eluting with a gradient of 0.5% MeOH/DCM to 10% MeOH/DCM to give N-(4-chlorophenethyl)-1H-indazole-5-carboxamide (0.165 g, 42%).

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over MgSO4
  4. customThe crude product was purified over silica gel on a Biotage Horizon high-performance flash chromatography system (25+M silica gel cartridge)
  5. washeluting with a gradient of 0.5% MeOH/DCM to 10% MeOH/DCM

Sources & evidence

ORD record
ord-d085218db49744c9a61ba85748e41c2d
Source dataset
uspto-grants-2013_01
Patent number
US08362056B2

Reaction notes

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