Oxalyl chloride → 2-Ethyl-4-methoxybenzothiazole-7-carboxylic acid (2-methyl-2H-pyrazol-3-yl)amide

HRID 427298Notes

Reaction equation

HRID 427298 reaction equation
[CH2:1]([C:3]1[S:4][C:5]2[C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=[C:8]([O:15][CH3:16])[C:6]=2[N:7]=1)[CH3:2].C(Cl)(=O)C(Cl)=O.[CH3:23][N:24]1[C:28]([NH2:29])=[CH:27][CH:26]=[N:25]1>CN(C)C=O.ClCCl.C(N(CC)CC)C>[CH3:23][N:24]1[C:28]([NH:29][C:12]([C:11]2[C:5]3[S:4][C:3]([CH2:1][CH3:2])=[N:7][C:6]=3[C:8]([O:15][CH3:16])=[CH:9][CH:10]=2)=[O:14])=[CH:27][CH:26]=[N:25]1

Participants

7

Reactant 3

HCID 65578Oxalyl chlorideHCID 1369272-Methyl-2H-pyrazol-3-ylamineHCID 183570002-Ethyl-4-methoxybenzothiazole-7-carboxylic acid

Product 1

HCID 99050072-Ethyl-4-methoxybenzothiazole-7-carboxylic acid (2-methyl-2H-pyrazol-3-yl)amideYield 30%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

Starting from 2-ethyl-4-methoxybenzothiazole-7-carboxylic acid (0.2 g), oxalyl chloride (0.15 ml), dichloromethane (20 ml) and dimethylformamide (1 drop), followed by 2-methyl-2H-pyrazol-3-ylamine (0.17 g), triethylamine (0.24 ml) and dichloromethane (40 ml). Purification by flash chromatography (eluent 10% methanol/dichloromethane) yielded the title compound as a yellow solid (0.08 g). TLC Rf 0.52 (10% methanol in dichloromethane), Mpt 185-186° C.

Workup

  1. customPurification by flash chromatography (eluent 10% methanol/dichloromethane)

Sources & evidence

ORD record
ord-abedb03cdb2f4a59b409fcb23003e02f
Source dataset
uspto-grants-2001_11
Patent number
US06313116B1

Reaction notes

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