HuagongsheHuagongshe Chemistry Print Report · For research reference only
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
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 5-Amino-1-methyl-1H-pyrazole-4-carbonitrile | HCID 219740 | — |
| Reactant | 2-(Piperidin-1-yl)-4-methoxybenzothiazole-7-carboxylic acid 4-nitrophenyl ester | HCID 69691118 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Sodium bis(trimethylsilyl)amide | HCID 2724254 | — |
| Product | 4Methoxy-2-(piperidin-1-yl)benzothiazole-7-carboylic acid (4-cyano-2-methyl-2h-pyrazol-3-yl)amide | HCID 10200779 | 75.5% |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06313116B1 |
| Source dataset | uspto-grants-2001_11 |
| ORD ID | ord-6a47be6d47214b01a96cdd685785e236 |
| Source note | uspto-grants-2001_11 |