Triethylamine → HCID 67951138、化合物

HRID 923642ノート

反応式

HRID 923642 の反応式
I[CH2:2][C:3]([N:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:7][CH2:6]1)=[O:4].[S:16]1(=O)[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2N=C1.CC[N:28]([CH2:31]C)CC.C([O-])([O-])=[O:34].[Cs+].[Cs+]>C(Cl)Cl>[O:34]=[C:31]1[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[S:16][N:28]1[CH2:2][C:3]([N:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:7][CH2:6]1)=[O:4]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 10796Cesium carbonateHCID 53400715BenzothiazolinoneHCID 67811489HCID 67811489、化合物

生成物 1

HCID 67951138HCID 67951138、化合物収率 63%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Ethyl 4-(2-iodoacetyl)piperazine-1-carboxylate (200 mg, 0.61 mmol) was added to a suspension of benzothiazolone 1 (102 mg, 0.67 mmol), Et3N (233 mg, 1.83 mmol) and Cs2CO3 (198 mg, 0.61 mmol) in anhydrous CH2Cl2 (8 mL) at room temperature. The mixture was stirred for 26 h, and washed with 1 M HCl(aq). The organic phase was dried over MgSO4, filtered, concentrated, and purified by flash chromatography on a silica gel column with elution of EtOAc/hexane (1:2) to give the title compound (134 mg, 63% yield). The purity of product was 99.3% as shown by HPLC on an HC-C18 column (Agilent, 4.6×250 mm, 5 μM), tR=11.87 min (gradients of 20-90% aqueous CH3CN in 20 min). C16H19N3O4S; white solid; mp 158-160° C.; 1H NMR (400 MHz, CDCl3) δ 8.09 (1H, dd, J=7.2 Hz, 0.8 Hz), 7.59 (1H, m), 7.53 (1H, dd, J=7.2, 0.8 Hz), 7.38 (1H, m), 4.69 (2H, s), 4.13 (2H, q, J=7.2 Hz), 3.60 (2H, m), 3.55 (2H, m), 3.48 (4H, m), 1.25 (3H, t, J=7.2 Hz); 13C NMR (100 MHz, CDCl3) δ 164.6, 154.6, 140.8, 131.8, 130.0, 126.4, 125.1, 122.9, 120.0, 61.9, 45.3, 45.0, 43.5 (2×), 42.2, 15.0; ESI-HRMS calcd for C16H19N3O4S: 372.0994. found: m/z 372.0992 [M+H]+.

後処理

  1. washwashed with 1 M HCl(aq)
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by flash chromatography on a silica gel column with elution of EtOAc/hexane (1:2)

出典と根拠

ORDレコード
ord-f15982f72d214fa3b23367c98640efb2
出典データセット
uspto-grants-2016_03
特許番号
US09278982B2

反応ノート

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