1-(2-Morpholinoethyl)-1,2,3,4-tetrahydroquinolin-6-amine → HCID 178511877、化合物

HRID 1922503ノート

反応式

HRID 1922503 の反応式
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][N:9]2[C:18]3[C:13](=[CH:14][C:15]([NH2:19])=[CH:16][CH:17]=3)[CH2:12][CH2:11][CH2:10]2)[CH2:3][CH2:2]1.I.[S:21]1[CH:25]=[CH:24][CH:23]=[C:22]1[C:26](SC)=[NH:27]>C(O)C.C(=O)(O)[O-].[Na+]>[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][N:9]2[C:18]3[C:13](=[CH:14][C:15]([NH:19][C:26]([C:22]4[S:21][CH:25]=[CH:24][CH:23]=4)=[NH:27])=[CH:16][CH:17]=3)[CH2:12][CH2:11][CH2:10]2)[CH2:3][CH2:2]1

参加物

5

反応物 2

HCID 284191151-(2-Morpholinoethyl)-1,2,3,4-tetrahydroquinolin-6-amineHCID 66704664Methyl thiophene-2-carbimidothioate hydroiodide

生成物 1

HCID 178511877HCID 178511877、化合物収率 59.5%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

A solution of compound 4 (0.23 g, 0.88 mmol) in dry ethanol (20 mL) was treated with methyl thiophene-2-carbimidothioate hydroiodide (0.502 g, 1.76 mmol) at room temperature and was stirred for 3 hours. The mixture was diluted with saturated sodium bicarbonate solution (50 mL) and was extracted with CH2Cl2 (100 mL). The organic layer was washed with brine (20 mL) and dried (Na2SO4). The concentrated crude product was subject to flash chromatography on silica gel using 5% methanol/CH2Cl2, which resulted in a brown foam, compound 64 (0.194 g, 59%). 1H NMR (CDCl3) δ 7.66 (d, J=3.9 Hz, 1H), 7.54 (d, J=4.5 Hz, 1H), 7.06 (dd, J=3.6, 5.1 Hz, 1H), 6.53 (s, 2H), 6.46 (s, 1H), 6.21 (brs, 2H), 3.57 (t, J=9.3 Hz, 4H), 3.24 (t, J=11.4 Hz, 2H), 3.65 (t, J=12.6 Hz, 2H), 2.45-2.41 (m, 6H), 1.88-1.80 (m, 2H); MS-ESI (m/z, %): 372 (11), 371 (MH+, 100), 258 (9); ESI-HRMS calculated for C20H27N4OS (MH+): Calculated: 371.1914, Observed: 371.1900.

後処理

  1. extractionwas extracted with CH2Cl2 (100 mL)
  2. washThe organic layer was washed with brine (20 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationThe concentrated crude product

出典と根拠

ORDレコード
ord-1224b01834274fbfa54e08de4ace1b8b
出典データセット
uspto-grants-2012_05
特許番号
US08173813B2

反応ノート

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