1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → methyl 5-[1-[4-[N'-(2-bromophenyl)ureido]-3-methoxyphenyl acetyl]-2-pyrrolidinylmethoxy]pyridine-2-carboxylate

HRID 354344노트

반응식

HRID 354344 반응식
[NH:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[CH2:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]([O:16][CH3:17])=[O:15])=[N:12][CH:13]=1.[Br: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>[Br: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:9]=[CH:10][C:11]([C:14]([O:16][CH3:17])=[O:15])=[N:12][CH:13]=2)=[O:36])=[CH:30][C:29]=1[O:38][CH3:39]

참가 물질

6

반응물 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23511835Methyl 5-(2-pyrrolidinyl)methoxypyridine-2-carboxylateHCID 23512062HCID 23512062, 화합물

생성물 1

HCID 69332272methyl 5-[1-[4-[N'-(2-bromophenyl)ureido]-3-methoxyphenyl acetyl]-2-pyrrolidinylmethoxy]pyridine-2-carboxylate수율 69.3%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6228Dimethylformamide용매

실험 절차

To a stirred mixture of methyl 5-(2-pyrrolidinyl)methoxypyridine-2-carboxylate (370 mg, 1.57 mmol), 4-[N′-(2-bromophenyl)ureido]-3-methoxyphenylacetic acid (595 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 5-[1-[4-[N′-(2-bromophenyl)ureido]-3-methoxypheny lacetyl]-2-pyrrolidinylmethoxy]pyridine-2-carboxylate (650 mg, 69%) as an amorphous solid. IR (KBr) n 3323, 1720, 1624, 1601, 1527 cm−1; 1H-NMR (CDCl3) δ1.22 and 2.00 (each m, 4 H), 3.48-4.55 (series of s and m, 13 H which contains amide-isomers), 6.93-8.82 (series of s and m, 12H which contains amide-isomers); MS (FAB) m/z 597 (M+−1) and 599 (M++1); Anal. Calcd. for C28H30BrN4O6.1.0×H2O: C, 54.55; H, 5.23; N, 9.09. Found: C, 54.13; H, 5.03; N, 9.33.

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-3d09795dee3643ceb54692a6b01c7733
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06756378B2

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