Huagongshe화공사 화학 정보 인쇄 보고서 · 연구 참고용
4-Methylmorpholine → 6-(4-Isopropyl-piperazine-1-carbonyl)-nicotinic acid methyl ester
참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|---|---|---|
| 반응물 | 4-Methylmorpholine | HCID 7972 | — |
| 반응물 | 5-(Methoxycarbonyl)pyridine-2-carboxylic acid | HCID 314992 | — |
| 반응물 | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| 반응물 | 1-Hydroxybenzotriazole hydrate | HCID 2796029 | — |
| 반응물 | 1-Isopropylpiperazine dihydrochloride | HCID 12268378 | — |
| 용매 | Dichloromethane | HCID 6344 | — |
| 생성물 | Ammonia | HCID 222 | 2% |
| 생성물 | 6-(4-Isopropyl-piperazine-1-carbonyl)-nicotinic acid methyl ester | HCID 44515774 | 149.8% |
반응 단계
To a solution of pyridine-2,5-dicarboxylic acid 5-methyl ester (1.00 g, 5.50 mmol) and 1-isopropyl-piperazine dihydrochloride (1.20 g, 6.10 mmol) in DCM (100 mL) was added 1-hydroxybenzotriazole hydrate (HOBt, 1.10 g, 8.30 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (EDC, 1.60 g, 8.30 mmol), and N-methyl morpholine (2.9 mL, 27.0 mmol). After 18 h, the reaction mixture was quenched with 1 N aq. NaHCO3 (50 mL) and extracted with DCM (3×50 mL). The organic layers were combined, dried (Na2SO4), and concentrated. Chromatography of the residue (SiO2; 2-5% 2 M NH3 in MeOH/DCM) gave the title compound (1.20 g, 74%).
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 특허 번호 | US07423147B2 |
| 출처 데이터셋 | uspto-grants-2008_09 |
| ORD ID | ord-8aa1265294d8459289e245119d19f9d8 |
| 출처 메모 | uspto-grants-2008_09 |