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4-(Morpholin-4-yl)benzene-1,2-diamine → 4-(2-(5-Nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl)-1H-benzo[d]imidazol-6-yl)morpholine

HRID 1047559
ノート
印刷プレビュー

反応式

HRID 1047559 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][O:14]1)[N:8]=[C:7]2[CH:19]=O)([O-:3])=[O:2].[O:21]1[CH2:26][CH2:25][N:24]([C:27]2[CH:28]=[C:29]([NH2:34])[C:30]([NH2:33])=[CH:31][CH:32]=2)[CH2:23][CH2:22]1.S(=O)(O)[O-].[Na+]>C1COCC1.Cl.C(OCC)(=O)C>[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][O:14]1)[N:8]=[C:7]2[C:19]1[NH:33][C:30]2[CH:31]=[CH:32][C:27]([N:24]3[CH2:23][CH2:22][O:21][CH2:26][CH2:25]3)=[CH:28][C:29]=2[N:34]=1)([O-:3])=[O:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 141123324-(Morpholin-4-yl)benzene-1,2-diamineHCID 23665763Sodium BisulfiteHCID 866732115-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-3-carbaldehyde

生成物 1

HCID 1363522614-(2-(5-Nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl)-1H-benzo[d]imidazol-6-yl)morpholine収率 50%

試薬・触媒・溶媒 3

HCID 313Hydrochloric Acid
触媒
HCID 8028Tetrahydrofuran溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

5-Nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-3-carbaldehyde (214 mg, 0.777 mmol) and 4-morpholinobenzene-1,2-diamine (150 mg, 0.777 mmol) were dissolved in dry THF (10 mL), and 2N HCl (1 drop) was added. The solution was heated at a gentle reflux for 30 min and then 1N sodium bisulfite (1 mL) was added. After overnight at reflux, the solution was cooled to room temperature, and diluted with ethyl acetate (40 mL). The mixture was washed with water and brine, dried over Na2SO4, and concentrated. Purification by flash chromatography (20% ethyl acetate/hexane) afforded the title compound as a pale yellow solid in a 50% yield. 1H NMR: (400 MHz, DMSO-d6): δ 9.49 (d, 1H, J=2.0 Hz), 8.41 (dd, 1H, J=2.0 and 9.2 Hz), 8.00 (d, 1H, J=9.2 Hz), 7.71 (m, 1H), 7.12 (m, 2H), 6.05 (dd, 1H, J=2.4 and 9.2 Hz), 4.75 (dd, 1H, J=2.4 and 6.8 Hz), 4.05 (m, 1H), 3.89 (m, 4H), 3.63 (m, 1H), 3.54-3.47 (m, 1H), 3.22 (m, 4H), 2.21 (m, 2H), 1.87 (m, 1H), 1.73 (m, 1H).

後処理

  1. temperatureThe solution was heated at
  2. temperaturea gentle reflux for 30 min
  3. temperatureAfter overnight at reflux
  4. washThe mixture was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customPurification by flash chromatography (20% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-8cbfcf2b3d6246d8b4c0d34ea4a3bf47
出典データセット
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08569511B2

反応ノート

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