Acetic Acid → 4-[1-Hydroxy-2,3-dihydro-1H-inden-4-yl)amino-6,7-dimethoxy-3-quinolinecarboxamide

HRID 1822854ノート

反応式

HRID 1822854 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][C:7]([C:15]([NH2:17])=[O:16])=[C:6]2[NH:18][C:19]1[CH:27]=[CH:26][CH:25]=[C:24]2[C:20]=1[CH2:21][CH2:22][C:23]2=[O:28].[BH4-].[Na+].C(O)(=O)C.C(=O)([O-])O.[Na+]>CO.O1CCCC1.O>[OH:28][CH:23]1[C:24]2[C:20](=[C:19]([NH:18][C:6]3[C:5]4[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=4)[N:9]=[CH:8][C:7]=3[C:15]([NH2:17])=[O:16])[CH:27]=[CH:26][CH:25]=2)[CH2:21][CH2:22]1

参加物

8

反応物 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 221702646,7-Dimethoxy-4-[(1-oxo-2,3-dihydro-1H-inden-4-yl)amino]-3-quinolinecarboxamide

生成物 1

HCID 221702254-[1-Hydroxy-2,3-dihydro-1H-inden-4-yl)amino-6,7-dimethoxy-3-quinolinecarboxamide

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

6,7-Dimethoxy-4-[(1-oxo-2,3-dihydro-1H-inden-4-yl)amino]-3-quinolinecarboxamide (0.062 g, 16.4 mmol) was dissolved in a mixture of methanol (7 ml), tetrahydrofuran (4 ml) and water (3 ml). Sodium borohydride was added in portions (3×5 mg) and during 5 min. After 20 min the reaction mixture was acidified with acetic acid and then made alkaline with saturated aqueous sodium hydrogencarbonate and evaporated. The residue was partitioned between water and ethyl acetate. The organic phase was washed twice with water and evaporated. The residue was dissolved in methanol and water was added. The title compound, which slowly precipitated, was filtered off and dried to give 40 mg (64%). 1H NMR (DMSO-d6): δ 10.68 (1H, s); 8.82 (1H, s); 8.20 (1H, bs); 7.55 (1H, bs); 7.22 (1H, s); 7.07 (1H, t, J 7.5 Hz); 7.04 (1H, t, J 7.4 Hz); 6.75 (1H, s); 6.63 (1H, d, J 7.5 Hz); 5.20 (1H, d, J 5.7 Hz); 5.01 (1H, q, J 6.2 Hz); 3.85 (3H, s); 3.26 (s, moisture signal overlapping); 2.72–2.63 (1H, m); 2.50–2.36 (m, solvent signal overlapping); 2.30–2.20 (1H, m) and 1.76–1.65 (1H, m).

後処理

  1. customevaporated
  2. customThe residue was partitioned between water and ethyl acetate
  3. washThe organic phase was washed twice with water
  4. customevaporated
  5. dissolutionThe residue was dissolved in methanol
  6. additionwater was added
  7. customThe title compound, which slowly precipitated
  8. filtrationwas filtered off
  9. customdried
  10. customto give 40 mg (64%)

出典と根拠

ORDレコード
ord-c1b931018edb4ea1b0f070455129bae0
出典データセット
uspto-grants-2006_05
特許番号
US07037925B2

反応ノート

読み込み中…