Sodium Iodide → HCID 5329446、化合物

HRID 1977615

反応式

HRID 1977615 の反応式
[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:7]=[N:8][N:9]3[CH:14]=[C:13]([C:15]4[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=4)[CH:12]=[N:11][C:10]=23)=[CH:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl.Cl[CH2:30][CH2:31][N:32]1[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1.[I-].[Na+]>CN(C=O)C.O>[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:7]=[N:8][N:9]3[CH:14]=[C:13]([C:15]4[CH:20]=[CH:19][C:18]([O:21][CH2:30][CH2:31][N:32]5[CH2:37][CH2:36][O:35][CH2:34][CH2:33]5)=[CH:17][CH:16]=4)[CH:12]=[N:11][C:10]=23)=[CH:2]1

参加物

7

反応物 4

HCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 226116713-(3-thienyl)-6-(4-hydroxyphenyl)-pyrazolo(1,5-A)pyrimidine

生成物 1

HCID 5329446HCID 5329446、化合物収率 64.7%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

A solution of example 3 (11 mg, 0.038 mmol), cesium carbonate (37 mg, 0.11 mmol), N-(2-chloroethyl)morpholine hydrochloride (7 mg, 0.11 mmol), and sodium iodide (0.013 mmol) in DMF (3 mL) was heated at 60° C. under argon for 16 h. The reaction mixture was then poured into water (25 mL) and washed with ethyl acetate (2×25 mL). The combined organics were dried (Na2SO4), concentrated, and purified by flash chromatography [50% Hexanes/CHCl3(NH3)] to give the title compound as a yellow solid [10 mg, 65%, mp =149-151° C., Rf=0.39 (100% CHCl3(NH3))]: 1H NMR (CDCl3) δ8.77 (d, 1H, J=2.2Hz), 8.75 (d, 1H, J=2.2Hz), 8.36 (s, 1H), 7.90 (dd, 1H, J=2.9, 1.3 Hz), 7.69 (dd, 1H, J=4.9, 1.3Hz), 7.52 (d, 2 H, J=8.8Hz), 7.43 (d, 1H, J=4.9, 2.9Hz), 7.06 (d, 2 H, J=8.8Hz), 4.18 (t, 2 H, J=5.7Hz), 3.76 (t, 4 H, J=4.6Hz), 2.85 (t, 2 H, J=5.7 Hz), 2.61 (t, 4 H, J=4.6Hz); FAB MS (M++1) Anal Calcd. for C22H22N4O2S : C, 65.00; H, 5.46; N, 13.78. Found C, 64.98; H, 5.55; N, 14.02.

後処理

  1. washwashed with ethyl acetate (2×25 mL)
  2. dry with materialThe combined organics were dried (Na2SO4)
  3. concentrationconcentrated
  4. custompurified by flash chromatography [50% Hexanes/CHCl3(NH3)]

出典と根拠

ORDレコード
ord-031ce42381854690915db0d4b3d96272
出典データセット
uspto-grants-2001_05
特許番号
US06235741B1

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