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

HRID 1830742ノート

反応式

HRID 1830742 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
65 °C

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-c60da704b1274246b59038de33df6966
出典データセット
uspto-grants-2006_06
特許番号
US07067506B2

反応ノート

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