関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Methanol | HCID 887 | — |
| 反応物 | Trifluoroacetic acid | HCID 6422 | — |
| 反応物 | Thiourea | HCID 2723790 | — |
| 反応物 | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| 反応物 | Picolinate | HCID 6920223 | — |
| 反応物 | Tert-butyl4-[3-amino-4-(methylamino)phenoxy]pyridine-2-carboxylate | HCID 22040526 | — |
| 溶媒 | Dichloromethane | HCID 6344 | — |
| 溶媒 | Tetrahydrofuran | HCID 8028 | — |
| 生成物 | 2-{[4-(Dimethylamino)phenylamino)-1-methylbenzimidazol-5-yloxy)-pyridine-2-carboxylic acid | HCID 86617166 | — |
反応手順
To tert-butyl4-[3-amino-4-(methylamino)phenoxy]pyridine-2-carboxylate (1 eq) in methanol was added 4-(dimethylamino)benzeneisothiocyanate (1 eq) and stir at ambient temperature for 16 h. Formation of the corresponding thiourea was followed by LC/MS. The mixture was then concentrated and to it was added tetrahydrofuran and 1-ethyl-(3-dimethylaminopropyl)carbodimidehydrochloride (2 eq) and stir at ambient temperature for 16 h. tert-butyl4-(2-{[4-dimethylamino)phenyl]amino)-1-methylbenzimidazol-5-yloxy)pyridine-2-carboxylate crashes out of the reaction mixture. To it in methylene chloride was added trifluoroacetic acid and stirred at ambient temperature overnight. Resulting 4-(2-{[4-dimethylamino)phenylamino)-1-methylbenzimidazol-5-yloxy)pyridine-2-carboxylic acid was purified by preparative chromatography. MS: MH+=403.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US07728010B2 |
|---|
| 出典データセット | uspto-grants-2010_06 |
|---|
| ORD ID | ord-d628560064ed4f8b9b216bd5fa493048 |
|---|
| 出典メモ | uspto-grants-2010_06 |
|---|
