Hydrochloric Acid → 4-(5-amino-3-tert-butyl-pyrazol-1-yl)-2-methyl-N-(2-morpholin-4-yl-ethyl)benzenesulfonamide

HRID 221874ノート

反応式

HRID 221874 の反応式
C(=[N:14][NH:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([NH:25][CH2:26][CH2:27][N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)(=[O:24])=[O:23])=[C:18]([CH3:34])[CH:17]=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH3:35][C:36]([CH3:43])([CH3:42])[C:37](=O)[CH2:38][C:39]#[N:40].Cl>C(O)C>[NH2:40][C:39]1[N:15]([C:16]2[CH:21]=[CH:20][C:19]([S:22]([NH:25][CH2:26][CH2:27][N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)(=[O:24])=[O:23])=[C:18]([CH3:34])[CH:17]=2)[N:14]=[C:37]([C:36]([CH3:43])([CH3:42])[CH3:35])[CH:38]=1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 536301814-(N'-benzhydrylidenehydrazino)-2-methyl-N-(2-morpholin-4-yl-ethyl)benzene sulfonamide

生成物 1

HCID 536301804-(5-amino-3-tert-butyl-pyrazol-1-yl)-2-methyl-N-(2-morpholin-4-yl-ethyl)benzenesulfonamide収率 91%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of 4-(N′-benzhydrylidene-hydrazino)-2-methyl-N-(2-morpholin-4-yl-ethyl)-benzene sulfonamide (1.00 g, 2.09 mmol) and 4,4-dimethyl-3-oxopentanenitrile (392 mg, 3.13 mmol, 1.5 eq) in anhydrous ethanol (10.5 mL, 0.2 M) was added p-toluenebenzene sulfonic acid (402 mg, 4.18 mmol, 2.0 eq), and the reaction mixture was stirred at reflux under nitrogen. After 18 h, concentrated HCl (2 mL) was added and the reaction mixture was stirred at reflux under nitrogen for an additional 4 h. The reaction mixture was cooled to room temperature and concentrated at reduced pressure. The residue was partitioned between EtOAc (500 mL) and aqueous saturated NaHCO3 solution (300 mL). The organic layer was washed with water and brine, dried over Na2SO4, and concentrated at reduced pressure. The residue was purified by MPLC (70% to 90% EtOAc/hexane) to give 799 mg (91%) of the desired product. 1H-NMR (DMSO-d6) δ 7.85 (d, J=8.4 Hz, 1H), 7.61 to 7.55 (m, 3H), 5.40 (s, 1H), 5.38 (broad s, 2H), 3.46 (t, J=4.5 Hz, 4H), 2.88 (q, J=6.0 Hz, 2H), 2.60 (s, 3H), 2.27 to 2.18 (m, 6H), 1.20 (s, 9H); MS LC-MS [M+H]+=422, RT=1.95 min.

後処理

  1. temperatureat reflux under nitrogen
  2. stirringthe reaction mixture was stirred
  3. temperatureat reflux under nitrogen for an additional 4 h
  4. concentrationconcentrated at reduced pressure
  5. customThe residue was partitioned between EtOAc (500 mL) and aqueous saturated NaHCO3 solution (300 mL)
  6. washThe organic layer was washed with water and brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated at reduced pressure
  9. customThe residue was purified by MPLC (70% to 90% EtOAc/hexane)

出典と根拠

ORDレコード
ord-a9cd95dfc8ea46bfbeff1368da15bba3
出典データセット
uspto-grants-2012_06
特許番号
US08207166B2

反応ノート

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