Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 6-Methoxy-m-toluenesulfonyl chloride | HCID 145149 | — |
| Reactant | N-[6-(5-Amino-6-chloro-3-pyridinyl)-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-yl]-2-methyl-1,3-thiazole-4-carboxamide | HCID 58255741 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Pyridine | HCID 1049 | — |
| Product | HCID 44539934 | HCID 44539934 | 64.3% |
Reaction Steps
N-[6-(5-Amino-6-chloro-3-pyridinyl)-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-yl]-2-methyl-1,3-thiazole-4-carboxamide (50 mg) was dissolved in pyridine (1 ml) and 5-methyl-2-(methyloxy)benzenesulfonyl chloride (35 mg) was added. The reaction was stirred at RT overnight. Further 5-methyl-2-(methyloxy)benzenesulfonyl chloride (35 mg) was added and the reaction was stirred at RT for 4 h. DMAP (3 mg) followed by 5-methyl-2-(methyloxy)benzenesulfonyl chloride (20 mg) was added and the reaction was stirred at RT overnight. The reaction was neutralised with 2M HCl (aq) and extracted into DCM. The DCM was evaporated and the residue was dissolved in DMSO:methanol (1 ml, 8:1, v/v) and purified by MDAP (method E). The desired fraction was evaporated to dryness and methanol (3 ml) and a few drops of 2M HCl (aq) were added and the reaction stirred for 2 h. The reaction was evaporated to dryness to give title compound (39 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08163743B2 |
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| Source dataset | uspto-grants-2012_04 |
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| ORD ID | ord-81b7af10fbd046d293c36bb2d61f6da6 |
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| Source note | uspto-grants-2012_04 |
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