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Hydrazine hydrate (1:1) → HCID 178432049、化合物

HRID 1188792
ノート
印刷プレビュー

反応式

HRID 1188792 の反応式
O.[NH2:2]N.[Cl:4][C:5]1[C:10]([Cl:11])=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:12][N:13]1[C:17]2[CH:18]=[C:19]([N:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)[CH:20]=[C:21]([C:22](/[N:24]=[CH:25]/[N:26](C)C)=O)[C:16]=2[N:15]=[C:14]1[CH3:35].C([O-])(O)=O.[Na+]>C(O)(=O)C>[Cl:4][C:5]1[C:10]([Cl:11])=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:12][N:13]1[C:17]2[CH:18]=[C:19]([N:29]3[CH2:30][CH2:31][O:32][CH2:33][CH2:34]3)[CH:20]=[C:21]([C:22]3[N:24]=[CH:25][NH:26][N:2]=3)[C:16]=2[N:15]=[C:14]1[CH3:35]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 24654Hydrazine hydrate (1:1)HCID 516892Sodium BicarbonateHCID 178432295HCID 178432295、化合物

生成物 1

HCID 178432049HCID 178432049、化合物収率 53%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
130 °C

実験手順

Hydrazine monohydrate (2 mL) was added to a solution of 1-[(2,3-dichlorophenyl)methyl]-N-[(1E)-(dimethylamino)methylidene]-2-methyl-6-(4-morpholinyl)-1H-benzimidazole-4-carboxamide (220 mg, 0.46 mmol) in acetic acid (5 mL) and stirred at 130° C. for 20 min. The reaction mixture was cooled to rt and poured into saturated NaHCO3 solution (15 mL). The mixture was extracted with DCM (30 mL×3). The combined organic layers were dried over MgSO4, filtered and concentrated. The resulting residue was purified by silica gel chromatography eluted with DCM:MeOH=30:1 to give the desired product (110 mg, 53%), as a white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 2.50 (s, 3H), 3.12 (t, 4H, J=4.8 Hz), 3.75 (t, 4H, J=4.8 Hz), 5.62 (s, 2H), 6.36 (d, 1H, J=8.1 Hz), 7.21 (s, 1H), 7.27 (t, 1H, J=8.1 Hz), 7.54 (s, 1H), 7.61 (d, 1H, J=8.1 Hz), 8.08 (s, 1H), 13.80 (s, 1H); LC-MS: m/e=443 [M+1]+.

後処理

  1. temperatureThe reaction mixture was cooled to rt
  2. extractionThe mixture was extracted with DCM (30 mL×3)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting residue was purified by silica gel chromatography
  7. washeluted with DCM

出典と根拠

ORDレコード
ord-c3835725cc3445b18f3113beb33b41d2
出典データセット
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08674090B2

反応ノート

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