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

HRID 427303Notes

Reaction equation

HRID 427303 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[C:8]#[N:9].[N+](C1C=CC([O:19][C:20]([C:22]2[C:30]3[S:29][C:28]([N:31]4[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]4)=[N:27][C:26]=3[C:25]([O:37][CH3:38])=[CH:24][CH:23]=2)=O)=CC=1)([O-])=O>CN(C)C=O.C[Si](C)(C)[N-][Si](C)(C)C.[Na+].O1CCCC1>[C:8]([C:3]1[CH:4]=[N:5][N:6]([CH3:7])[C:2]=1[NH:1][C:20]([C:22]1[C:30]2[S:29][C:28]([N:31]3[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]3)=[N:27][C:26]=2[C:25]([O:37][CH3:38])=[CH:24][CH:23]=1)=[O:19])#[N:9]

Participants

6

Reactant 2

HCID 2197405-Amino-1-methyl-1H-pyrazole-4-carbonitrileHCID 696911182-(Piperidin-1-yl)-4-methoxybenzothiazole-7-carboxylic acid 4-nitrophenyl ester

Product 1

HCID 102007794Methoxy-2-(piperidin-1-yl)benzothiazole-7-carboylic acid (4-cyano-2-methyl-2h-pyrazol-3-yl)amideYield 75.5%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 2724254Sodium bis(trimethylsilyl)amideSolvent

Procedure

Starting from 5-amino-1-methyl-1H-pyrazole-4-carbonitrile (125 mg) in dimethyl formamide (10 ml), sodium hexamethyldisilazide in tetrahydrofuran (1.1 ml, 1.0 M), and 4-methoxy-2-(piperidin-1-yl)benzothiazole-7-carboxylic acid 4-nitrophenyl ester (210 mg). Purification by flash chromatography (eluent 5% methanol in dichloromethane) followed by trituration with ethyl acetate yielded the title compound as an off-white solid (152 mg). TLC Rf 0.48 (ethyl acetate); Mpt 290-291° C.

Workup

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

Sources & evidence

ORD record
ord-6a47be6d47214b01a96cdd685785e236
Source dataset
uspto-grants-2001_11
Patent number
US06313116B1

Reaction notes

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