Diisopropylethylamine → N-(4-tert-butylbenzyl)-N'-(1,3-dimethyl-5-isoquinolinyl)urea

HRID 586003

反応式

HRID 586003 の反応式
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][N:12]=[C:13]=[O:14])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:15][C:16]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:17]=1[CH:18]=[C:19]([CH3:27])[N:20]=[C:21]2[CH3:26].CCN(C(C)C)C(C)C>C1(C)C=CC=CC=1>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH2:11][NH:12][C:13]([NH:15][C:16]2[CH:25]=[CH:24][CH:23]=[C:22]3[C:17]=2[CH:18]=[C:19]([CH3:27])[N:20]=[C:21]3[CH3:26])=[O:14])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 220422271-Tert-butyl-4-(isocyanatomethyl)benzeneHCID 223376241,3-Dimethylisoquinolin-5-amine

生成物 1

HCID 10473764N-(4-tert-butylbenzyl)-N'-(1,3-dimethyl-5-isoquinolinyl)urea

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

The product from Example 186A (3.42 mmol) in toluene (12 mL) was treated with 5-amino-1,3-dimethylisoquinoline (245 mg, 1.42 mmol) and DIEA (5 mL). The mixture was heated at 800 for 3 hours, cooled to room tempoerature, and filtered. The precipitate thus obtained was purified by silica gel chromatography (97:3 CH2Cl2:CH3OH to 95:5 CH2Cl2:CH3OH) to provide the title compound. The corresponding hydrochloride salt was prepared by treatment with methanolic HCl. 1H NMR (300 MHz, DMSO-d6) δ 8.55 (s, 1H), 8.21 (d, 1H, J=7.1 Hz), 7.78 (d, 1H, 8.5 Hz), 7.59 (s, 1H), 7.48 (t, 1H, J=8.0 Hz), 7.36-7.40 (m, 2H), 7.27-7.29 (m, 2H), 6.98 (m, 1H), 4.31 (d, 2H, J=5.8 Hz), 2.84 (s, 3H), 2.58 (s, 3H), 1.28 (s, 9H); MS (ESI+) m/z 362 (M+H).

後処理

  1. temperatureThe mixture was heated at 800 for 3 hours
  2. temperaturecooled to room tempoerature
  3. filtrationfiltered
  4. customThe precipitate thus obtained
  5. customwas purified by silica gel chromatography (97:3 CH2Cl2:CH3OH to 95:5 CH2Cl2:CH3OH)

出典と根拠

ORDレコード
ord-ba0357e825bf452fa5e008fbcba3cf2b
出典データセット
uspto-grants-2005_08
特許番号
US06933311B2

関連ノート

読み込み中…