Hydrochloric Acid → 3-[3-(5-Isoquinolinylsulfonyloxy)-5-methylphenoxy]propoxyamine

HRID 1977948ノート

反応式

HRID 1977948 の反応式
[CH:1]1[C:10]2[C:5](=[C:6]([S:11]([O:14][C:15]3[CH:16]=[C:17]([CH:34]=[C:35]([CH3:37])[CH:36]=3)[O:18][CH2:19][CH2:20][CH2:21][O:22][N:23]3C(=O)C4=CC=CC=C4C3=O)(=[O:13])=[O:12])[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.[BH4-].[Na+].Cl.[OH-].[Na+]>C(O)C.O.O1CCCC1>[CH:1]1[C:10]2[C:5](=[C:6]([S:11]([O:14][C:15]3[CH:16]=[C:17]([CH:34]=[C:35]([CH3:37])[CH:36]=3)[O:18][CH2:19][CH2:20][CH2:21][O:22][NH2:23])(=[O:13])=[O:12])[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 22722554n-[3-[3-(5-Isoquinolinylsulfonyloxy)-5-methylphenoxy]propoxy]phthalimide

生成物 1

HCID 227226933-[3-(5-Isoquinolinylsulfonyloxy)-5-methylphenoxy]propoxyamine収率 26%

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of N-[3-[3-(5-isoquinolinylsulfonyloxy)-5-methylphenoxy]propoxy]phthalimide (570 mg, 1.1 mmol), as prepared in the preceding step, in ethanol (20 mL), tetrahydrofuran (10 mL), and water (10 mL) was added sodium borohydride (230 mg, 6.0 mmol). The reaction mixture was stirred at ambient temperature overnight. The mixture was acidified (pH 1-2) with 2 N HCl and heated at 50° C. for 2 hours. After cooling to room temperature, 2 N NaOH was added to adjust the pH to 8-9. The mixture was extracted with ethyl acetate (3×50 mL). The combined organic extracts were washed with brine (50 mL) and dried over Na2SO4. After removing the solvent, the residue was purified by flash column chromatography (ethyl acetate) to give the title compound as a colorless oil (110 mg, 26%). 1H-NMR (300 MHz, CDCl3) δ9.42 (s, 1H), 8.81 (d, J=6.1 Hz, 1H), 8.54 (d, J=6.1 Hz, 1H), 8.33 (m, 2H), 7.67 (t, J=7.8 Hz, 1H), 6.55 (s, 1H), 6.28 (s, 1H), 6.23 (s, 1H), 3.81 (t, J=6.3 Hz, 2H), 3.74 (t, J=6.1 Hz, 2H), 2.15 (s, 3H), 1.94 (m, 2H). Mass spectrum (MALDI-TOF, α-cyano-4-hydroxycinnamic acid matrix) calcd. for C19H20N2O5S: 389.1 (M+H), 411.1 (M+Na). Found: 389.3, 411.1.

後処理

  1. temperatureheated at 50° C. for 2 hours
  2. temperatureAfter cooling to room temperature
  3. extractionThe mixture was extracted with ethyl acetate (3×50 mL)
  4. washThe combined organic extracts were washed with brine (50 mL)
  5. dry with materialdried over Na2SO4
  6. customAfter removing the solvent
  7. customthe residue was purified by flash column chromatography (ethyl acetate)

出典と根拠

ORDレコード
ord-5089bb5ef1714d3ba62f892ba588b957
出典データセット
uspto-grants-2001_05
特許番号
US06235778B1

反応ノート

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