HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methylamine → 1049025-94-6
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methylamine | HCID 6329 | — |
| Reactant | Thionyl Chloride | HCID 24386 | — |
| Reactant | Oxalyl chloride | HCID 65578 | — |
| Reactant | 5-Chloropyrazinoic acid | HCID 465472 | — |
| Reactant | 5-Chloropyrazine-2-carbonyl chloride | HCID 15215743 | — |
| Reactant | HCID 66699176 | HCID 66699176 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 1049025-94-6 | HCID 59276991 | — |
Reaction Steps
Methyl 5-chloro-2-pyridazinecarboxylate (CAS #33332-25-1) is hydrolyzed to the corresponding carboxylic acid, 5-chloropyrazine-2-carboxylic acid. This acid is then converted to the corresponding acid chloride, 5-chloropyrazine-2-carbonyl chloride, by treatment with either thionyl chloride or oxalyl chloride. This acid chloride is then treated with a 2 M solution of methylamine in tetrahydrofuran to provide 5-chloro-N-methylpyrazine-2-carboxamide. The procedure of Example 48 is then repeated, substituting 5-chloro-N-methylpyrazine-2-carboxamide in place of 6-chloro-N-methyl-3-pyridinecarboxamide to give (R)—N-methyl-5-(2-(3-(piperidin-1-yl)pyrrolidin-1-yl)benzo[d]thiazol-6-yloxy)pyrazine-2-carboxamide.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08153813B2 |
| Source dataset | uspto-grants-2012_04 |
| ORD ID | ord-7c5d466bc0644dbea8427b8cea90c682 |
| Source note | uspto-grants-2012_04 |