5-Amino-1-methyl-1H-pyrazole-4-carbonitrile → HCID 10117651, compound

HRID 427304Notes

Reaction equation

HRID 427304 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[C:8]#[N:9].C[Si](C)(C)[N-][Si](C)(C)C.[Na+].[N+](C1C=CC([O:29][C:30]([C:32]2[C:40]3[S:39][C:38]([N:41]4[CH2:46][CH2:45][N:44]([C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[CH2:43][CH2:42]4)=[N:37][C:36]=3[C:35]([O:54][CH3:55])=[CH:34][CH:33]=2)=O)=CC=1)([O-])=O>O1CCCC1>[C:8]([C:3]1[CH:4]=[N:5][N:6]([CH3:7])[C:2]=1[NH:1][C:30]([C:32]1[C:40]2[S:39][C:38]([N:41]3[CH2:46][CH2:45][N:44]([C:47]([O:49][C:50]([CH3:51])([CH3:52])[CH3:53])=[O:48])[CH2:43][CH2:42]3)=[N:37][C:36]=2[C:35]([O:54][CH3:55])=[CH:34][CH:33]=1)=[O:29])#[N:9]

Participants

5

Reactant 3

HCID 2197405-Amino-1-methyl-1H-pyrazole-4-carbonitrileHCID 2724254Sodium bis(trimethylsilyl)amideHCID 69691230HCID 69691230, compound

Product 1

HCID 10117651HCID 10117651, compoundYield 107.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Starting from 5-amino-1-methyl-1H-pyrazole-4-carbonitrile (119 mg) in dimethyl fonnamide (10 ml), sodium hexamethyldisilazide in tetrahydrofuran (0.97 ml, 1.0 M), 2-(4-tert-butoxycarbonylpiperazin-1-yl)-4-methoxybenzothiazole-7-carboxylic acid 4-nitrophenyl ester (250 mg). Purification by flash chromatography (eluent 5% methanol in dichloromethane) followed by trituration with diethyl ether yielded the title compound as a pale yellow solid (260 mg). TLC Rf 0.48 (ethyl acetate); Mpt 231-232° C.

Workup

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

Sources & evidence

ORD record
ord-b9f389cc63e94f3db3332f53b7d50ef0
Source dataset
uspto-grants-2001_11
Patent number
US06313116B1

Reaction notes

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