Oxalyl chloride → 2-Cyclopropyl-4-methoxybenzothiazole-7-carboxylic acid (3,5-dimethylisoxazol-4-yl)amide

HRID 427296Notes

Reaction equation

HRID 427296 reaction equation
[CH:1]1([C:4]2[S:5][C:6]3[C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=[C:9]([O:16][CH3:17])[C:7]=3[N:8]=2)[CH2:3][CH2:2]1.C(Cl)(=O)C(Cl)=O.[CH3:24][C:25]1[C:29]([NH2:30])=[C:28]([CH3:31])[O:27][N:26]=1>CN(C)C=O.ClCCl.C(N(CC)CC)C>[CH3:24][C:25]1[C:29]([NH:30][C:13]([C:12]2[C:6]3[S:5][C:4]([CH:1]4[CH2:2][CH2:3]4)=[N:8][C:7]=3[C:9]([O:16][CH3:17])=[CH:10][CH:11]=2)=[O:15])=[C:28]([CH3:31])[O:27][N:26]=1

Participants

7

Reactant 3

HCID 65578Oxalyl chlorideHCID 1820404-Amino-3,5-dimethylisoxazoleHCID 183570082-Cyclopropyl-4-methoxybenzothiazole-7-carboxylic acid

Product 1

HCID 99679332-Cyclopropyl-4-methoxybenzothiazole-7-carboxylic acid (3,5-dimethylisoxazol-4-yl)amideYield 24.3%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

Starting from 2-cyclopropyl-4-methoxybenzothiazole-7-carboxylic acid (0.20 g), oxalyl chloride (0.11 ml), dichloromethane (30 ml) and dimethylformamide (1 drop), followed by 3,5-dimethylisoxazol-4-amine (0.20 g), triethylamine (0.22 ml) and dichloromethane (30 ml). Purification by flash chromatography (eluent 50% ethyl acetate/heptane) yielded the title compound as a white solid (0.067 g). TLC Rf 0.33 (ethyl acetate); Mpt 196-197° C.

Workup

  1. customPurification by flash chromatography (eluent 50% ethyl acetate/heptane)

Sources & evidence

ORD record
ord-fceccac26d6046be833bb838bde46541
Source dataset
uspto-grants-2001_11
Patent number
US06313116B1

Reaction notes

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