5-Amino-1-methyl-1H-pyrazole-4-carbonitrile → 4Methoxy-2-(morpholin-4-yl)-benzothiazole-7-carboxylic acid (4-cyano-2-methyl-2H-pyrazol-3-yl)amide

HRID 427300

Reaction equation

HRID 427300 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)[S:11][C:7]=2[C:6]([C:18]([OH:20])=O)=[CH:5][CH:4]=1.[NH2:21][C:22]1[N:26]([CH3:27])[N:25]=[CH:24][C:23]=1[C:28]#[N:29]>CN(C)C=O.ClCCl>[C:28]([C:23]1[CH:24]=[N:25][N:26]([CH3:27])[C:22]=1[NH:21][C:18]([C:6]1[C:7]2[S:11][C:10]([N:12]3[CH2:13][CH2:14][O:15][CH2:16][CH2:17]3)=[N:9][C:8]=2[C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[O:20])#[N:29]

Participants

5

Reactant 2

HCID 2197405-Amino-1-methyl-1H-pyrazole-4-carbonitrileHCID 183569914-Methoxy-2-(morpholin-4-yl)benzothiazole-7-carboxylic acid

Product 1

HCID 102225134Methoxy-2-(morpholin-4-yl)-benzothiazole-7-carboxylic acid (4-cyano-2-methyl-2H-pyrazol-3-yl)amideYield 11.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Starting with 4-methoxy-2-(morpholin-4-yl)benzothiazole-7-carboxylic acid (0.13 g) oxalyl chloride (0.10 ml), dichloromethane (10 ml) and dimethylformamide (1 drop), followed by 5-amino-1-methyl-1H-pyrazole-4-carbonitrile (0.11 g), sodium hexamethyldisilylamine (1.0M in tetrahydrofuran, 0.88 ml) and dichloromethane (10 ml). Purification by flash chromatography (eluent ethyl acetate) yielded the title compound as an off-white solid (0.02 g). TLC Rf 0.45 (ethyl acetate); Mpt 299-300° C.

Workup

  1. customPurification by flash chromatography (eluent ethyl acetate)

Sources & evidence

ORD record
ord-14080d70c0864b4f8ef496b3854154db
Source dataset
uspto-grants-2001_11
Patent number
US06313116B1

Linked notes

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