1,2-Dichloroethane → N-Methyl-N-(1-methyl-1H-indazol-3-ylmethyl)-2-phenylbenzamide

HRID 1581689

Reaction equation

HRID 1581689 reaction equation
[C:1]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:2]([C:7]([OH:9])=O)=[CH:3][CH:4]=[CH:5][CH:6]=1.[CH3:16][N:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19]([CH2:26][NH:27][CH3:28])=[N:18]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.O.C(N(CC)CC)C>CN(C=O)C>[CH3:28][N:27]([CH2:26][C:19]1[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:17]([CH3:16])[N:18]=1)[C:7](=[O:9])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

8

Reactant 6

HCID 111,2-DichloroethaneHCID 962WaterHCID 8471TriethylamineHCID 70357o-Phenylbenzoic acidHCID 757711-HydroxybenzotriazoleHCID 7537473N-Methyl-N-[(1-methyl-1H-indazol-3-yl)methyl]amine

Product 1

HCID 9798740N-Methyl-N-(1-methyl-1H-indazol-3-ylmethyl)-2-phenylbenzamideYield 62.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-biphenylcarboxylic acid (198 mg, 1 mmole), 1-methyl-3-(methylaminomethyl)-1H-indazole (210 mg, 1.2 mmole), EDC (230 mg, 1.2 mmole), HOBt.H2O (162 mg, 1.2 mmole), and triethylamine (0.28 mL, 2.0 mmole) in DMF (5 mL) was stirred at RT. After 18 hr, the reaction was concentrated to dryness, and the residue was purified by flash chromatography on silica gel (45% EtOAc/hexanes). The title compound (221 mg, 62%) was obtained as a white solid: MS (ES) m/e 356 (M+H)+.

Workup

  1. concentrationthe reaction was concentrated to dryness
  2. customthe residue was purified by flash chromatography on silica gel (45% EtOAc/hexanes)

Sources & evidence

ORD record
ord-9fd9e588799648d3bdebc4746bc4b3d8
Source dataset
uspto-grants-2004_05
Patent number
US06730684B1

Linked notes

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