Oxalyl chloride → 4-(3-Methyl-1-pyrazolyl)-2-chlorobenzoyl chloride

HRID 1635819Notes

Reaction equation

HRID 1635819 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N:8]2[CH:12]=[CH:11][C:10]([CH3:13])=[N:9]2)[CH:5]=[CH:4][C:3]=1[C:14](N1C2C=CC=CC=2CN2C(C)=CC=C2C1)=[O:15].[Cl:31]C1C=C(N2C=CC(C)=N2)C=CC=1C(O)=O.C(Cl)(=O)C(Cl)=O>CN(C)C=O.ClCCl>[Cl:1][C:2]1[CH:7]=[C:6]([N:8]2[CH:12]=[CH:11][C:10]([CH3:13])=[N:9]2)[CH:5]=[CH:4][C:3]=1[C:14]([Cl:31])=[O:15]

Participants

6

Reactant 3

HCID 65578Oxalyl chlorideHCID 9802041[2-Chloro-4-(3-methylpyrazol-1-yl)-phenyl]-(3-methyl-5H,11H-pyrrolo[2,1-c][1,4]-benzodiazepin-10-yl)-methanoneHCID 108474542-Chloro-4-(3-methyl-1H-pyrazol-1-yl)benzoic acid

Product 1

HCID 226054464-(3-Methyl-1-pyrazolyl)-2-chlorobenzoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

Step e) [2-Chloro-4-(3-methylpyrazol-1-yl)-phenyl]-(3-methyl-5H,11H-pyrrolo[2,1-c][1,4]-benzodiazepin-10-yl)-methanone: A mixture of 2-chloro-4-(3-methylpyrazol-1-yl)-benzoic acid (0.18 g) from step c) of Example 10, oxalyl chloride (0.18 g) and one drop of dimethylformamide in dichloromethane (10 ml), was stirred at room temperature for 18 hours. The mixture was concentrated in vacuo, and the residue was redissolved in dichloromethane and reconcentrated in vacuo to yield 2-chloro-4-(3-methyl-pyrazol-1-yl)-benzoyl chloride. A slurry of the acid chloride in dichloromethane (25 ml) was added dropwise to a solution of 10,11-dihydro-3-methyl-5H-pyrrolo[2,1-c][1,4]benzodiazepine (0.12 g) and diisopropylethylamine (0.10 g) in dichloromethane (25 ml). The mixture was stirred at room temperature for 18 h, and washed with water and saturated aqueous sodium bicarbonate. The organic phase was dried over anhydrous sodium sulfate and filtered through a short column of anhydrous sodium magnesium silicate. The solution was concentrated in vacuo and triturated with diethyl ether to yield 0.115 g of product as colorless crystals, m.p. 178-180° C., MS m/z: 417.3 (M+H)+, 833.3 (2M+H)+.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionthe residue was redissolved in dichloromethane

Sources & evidence

ORD record
ord-4886d97fc6e64387951228af5e30e0a0
Source dataset
uspto-grants-2003_01
Patent number
US06511974B1

Reaction notes

Loading…