Oxalyl chloride → 4-Methoxy-2-(piperidin-1-yl)benzothiazole-7-carboxylic acid (3,5-dimethyiisoxazol-4-yl)amide

HRID 427297Notes

Reaction equation

HRID 427297 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([N:12]3[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]3)[S:11][C:7]=2[C:6]([C:18]([OH:20])=O)=[CH:5][CH:4]=1.C(Cl)(=O)C(Cl)=O.[CH3:27][C:28]1[C:32]([NH2:33])=[C:31]([CH3:34])[O:30][N:29]=1>CN(C)C=O.ClCCl.C(N(CC)CC)C>[CH3:27][C:28]1[C:32]([NH:33][C:18]([C:6]2[C:7]3[S:11][C:10]([N:12]4[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]4)=[N:9][C:8]=3[C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[O:20])=[C:31]([CH3:34])[O:30][N:29]=1

Participants

7

Reactant 3

HCID 65578Oxalyl chlorideHCID 1820404-Amino-3,5-dimethylisoxazoleHCID 183569982-(Piperidin-1-yl)-4-methoxybenzothiazole-7-carboxylic acid

Product 1

HCID 102935314-Methoxy-2-(piperidin-1-yl)benzothiazole-7-carboxylic acid (3,5-dimethyiisoxazol-4-yl)amideYield 9.1%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

Starting from 4-methoxy-2(piperidin-1-yl)benzothiazole-7-carboxylic acid (0.24 g), oxalyl chloride (2.0 ml), dichloromethane (20 ml) and dimethylformamide (1 drop), followed by 3,5-dimethylisoxazol-4-amine (0.10 g), triethylamine (0.25 ml) and dichloromethane (20 ml). Purification by flash chromatography (eluent 5% methanol in dichloromethane) yielded the title compound as a white solid (29 mg). TLC Rf 0.49 (ethyl acetate); MS found M+1 387.

Workup

  1. customPurification by flash chromatography (eluent 5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-8286f2d80f70441c926202a8b4feda4a
Source dataset
uspto-grants-2001_11
Patent number
US06313116B1

Reaction notes

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