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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → methyl 2-[1-[4-[N'-(2-chlorophenyl)ureido]-3-methoxyphenyl acetyl]-2-pyrrolidinylmethoxy]pyridine-5-carboxylate

HRID 350407
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HRID 350407 반응식
[NH:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([O:16][CH3:17])=[O:15])=[CH:10][N:9]=1.[Cl:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[NH:25][C:26](=[O:40])[NH:27][C:28]1[CH:33]=[CH:32][C:31]([CH2:34][C:35](O)=[O:36])=[CH:30][C:29]=1[O:38][CH3:39].CCN=C=NCCCN(C)C.Cl>CN(C1C=CN=CC=1)C.CN(C=O)C>[Cl:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[NH:25][C:26](=[O:40])[NH:27][C:28]1[CH:33]=[CH:32][C:31]([CH2:34][C:35]([N:1]2[CH2:5][CH2:4][CH2:3][CH:2]2[CH2:6][O:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]([O:16][CH3:17])=[O:15])=[CH:10][N:9]=2)=[O:36])=[CH:30][C:29]=1[O:38][CH3:39]
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참가 물질

6

반응물 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23511785Methyl 2-(2-pyrrolidinyl)methoxypyridine-5-carboxylateHCID 235118674-[N'-(2-chlorophenyl)ureido]-3-methoxyphenylacetic acid

생성물 1

HCID 23512353methyl 2-[1-[4-[N'-(2-chlorophenyl)ureido]-3-methoxyphenyl acetyl]-2-pyrrolidinylmethoxy]pyridine-5-carboxylate수율 69.1%

시약·촉매·용매 2

HCID 14284
4-(Dimethylamino)pyridine
촉매
HCID 6228Dimethylformamide용매

실험 절차

To a stirred mixture of methyl 2-(2-pyrrolidinyl)methoxypyridine-5-carboxylate (370 mg, 1.57 mmol), 4-[N′-(2-chlorophenyl)ureido]-3-methoxyphenylacetic acid (525 mg, 1.57 mmol), 4-DMAP (230 mg, 1.88 mmol) in DMF (10 ml) was added EDC.HCl (360 mg, 1.88 mmol) at room temperature. The resulting mixture was stirred at room temperature for 20 hr. The mixture was pored into ice-water. The solid was collected, washed with water and air-dried. The crude solid was purified by silica-gel (30 ml) column chromatography with CHCl3-EtOH (98:2, v/v) as eluent and crystallized with Et2O to give methyl 2-[1-[4-[N′-(2-chlorophenyl)ureido]-3-methoxyphenyl acetyl]-2-pyrrolidinylmethoxy]pyridine-5-carboxylate (600 mg, 69%) as an amorphous solid. 1H-NMR (CDCl3) δ 0.21 and 2.01 (each m, 4 H), 3.45–4.50 (series of s and m, 13 H which contains amide-isomers), 6.58–8.83 (series of s and m, 12 H which contains amide-isomers)

후처리

  1. customThe solid was collected
  2. washwashed with water
  3. customair-dried
  4. customThe crude solid was purified by silica-gel (30 ml) column chromatography with CHCl3-EtOH (98:2
  5. customv/v) as eluent and crystallized with Et2O

출처 및 근거

ORD 기록
ord-b98e29df47704c25bca5007838abf7df
출처 데이터셋
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07179819B2

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