Triethylamine → 4-[3-(5-Methyl-pyrazin-2-yl)-ureido]-3-(pyridin-3-ylmethoxy)-benzoic acid methyl ester

HRID 1830742노트

반응식

HRID 1830742 반응식
[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([O:11][CH2:12][C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[CH:5]=1.C(N(CC)CC)C.ClC(Cl)(O[C:31](=[O:37])OC(Cl)(Cl)Cl)Cl.[CH3:39][C:40]1[N:41]=[CH:42][C:43]([NH2:46])=[N:44][CH:45]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C.O>[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:31]([NH:46][C:43]2[CH:42]=[N:41][C:40]([CH3:39])=[CH:45][N:44]=2)=[O:37])=[C:6]([O:11][CH2:12][C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[CH:5]=1

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 3132155-Methylpyrazin-2-amineHCID 433801884-Amino-3-(pyridin-3-ylmethoxy)-benzoic acid methyl ester

생성물 1

HCID 672560024-[3-(5-Methyl-pyrazin-2-yl)-ureido]-3-(pyridin-3-ylmethoxy)-benzoic acid methyl ester수율 47%

시약·촉매·용매 3

HCID 962Water용매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

반응 조건

온도
65 °C

실험 절차

To a stirred, cooled (about 0° C.) solution of 4-amino-3-(pyridin-3-ylmethoxy)-benzoic acid methyl ester (258 mg, 1.0 mmol) in toluene (3.0 mL) was added triethylamine (139 μL, 1.0 mmol) and triphosgene (98 mg, 0.33 mmol). After stirring for 30 minutes, 5-methyl-2-amino pyrazine (109 mg, 1.0 mmol) was added and the reaction was heated to 65 degrees C. The reaction was allowed to cool to room temperature, then diluted with ethyl acetate (50 mL) and water (50 mL). A precipitate formed which was filtered and dried under reduced pressure to yield the desired material as a white solid (47% yield). 1H-NMR (400 MHz, d6-DMSO) δ10.29 (s, 1H), 8.79 (s, 1H), 8.68 (d, 1H, 8.59 (br s, 1H), 8.48 (d, 1H), 7.70 (s, 1H), 7.62 (d, 1H), 7.51 (m, 1H), 5.32 (s, 2H), 3.88 (s, 3H), 2.32 (s, 3H).

후처리

  1. temperatureto cool to room temperature
  2. customA precipitate formed which
  3. filtrationwas filtered
  4. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-c60da704b1274246b59038de33df6966
출처 데이터셋
uspto-grants-2006_06
특허 번호
US07067506B2

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