Methanol → 1-methyl-6-(3-(tetrahydro-2H-pyran-2-yloxy)prop-1-ynyl)-1H-thieno[2,3-c][1,2]thiazin-4(3H)-one 2,2-dioxide

HRID 1070632ノート

反応式

HRID 1070632 の反応式
I[C:2]1[S:14][C:5]2[N:6]([CH3:13])[S:7](=[O:12])(=[O:11])[CH2:8][C:9](=[O:10])[C:4]=2[CH:3]=1.[CH2:15]([O:18][CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][O:20]1)[C:16]#[CH:17].CO>C1(C)C=CC=CC=1.C(N(CC)CC)C>[CH3:13][N:6]1[C:5]2[S:14][C:2]([C:17]#[C:16][CH2:15][O:18][CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][O:20]3)=[CH:3][C:4]=2[C:9](=[O:10])[CH2:8][S:7]1(=[O:12])=[O:11]

参加物

6

反応物 3

HCID 887MethanolHCID 98609Tetrahydro-2-(2-propynyloxy)-2H-pyranHCID 223971566-iodo-1-methyl-1H-thieno[2,3-c][1,2]thiazin-4(3H)-one 2,2-dioxide

生成物 1

HCID 223972121-methyl-6-(3-(tetrahydro-2H-pyran-2-yloxy)prop-1-ynyl)-1H-thieno[2,3-c][1,2]thiazin-4(3H)-one 2,2-dioxide収率 66%

試薬・触媒・溶媒 2

HCID 8471Triethylamine触媒HCID 1140Toluene溶媒

実験手順

To a stirring mixture of 6-iodo-1-methyl-1H-thieno[2,3-c][1,2]thiazin-4(3H)-one 2,2-dioxide (Preparation 34, 1.0 g), triethylamine (1.5 mL) CuI (13.8 mg), and tetrahydro-2-(2-propynyloxy)-2H-pyran (0.49 g) in toluene (50 mL) at ambient temperature is added tetrakis triphenylphosphine palladium (40 mg). The resulting mixture is stirred overnight at ambient temperature. MeOH (50 mL) is added, the mixture is stirred 20 min and the solvent is removed in vacuo. The residue is partitioned between 10% HCl/H2O/EtOAc (100 ml each), and the organic layer is separated. The solvent is removed in vacuo and the residue purified by flash column chromatography (4/1, hexanes/EtOAc) to afford 0.68 g (66%) of the title compound as a white solid. Physical characteristics: 1H NMR (CDCl3) δ1.52-1.86, 3.39, 3.55, 3.84, 4.21, 4.45, 4.81, 7.38; MS (ESI−) m/z 354 (M−H)−. Anal. Found: C, 50.70; H, 4.89; N, 3.95.

後処理

  1. stirringthe mixture is stirred 20 min
  2. customthe solvent is removed in vacuo
  3. customThe residue is partitioned between 10% HCl/H2O/EtOAc (100 ml each)
  4. customthe organic layer is separated
  5. customThe solvent is removed in vacuo
  6. customthe residue purified by flash column chromatography (4/1, hexanes/EtOAc)

出典と根拠

ORDレコード
ord-bbae09228bee4268904ec9df1a05ed0d
出典データセット
uspto-grants-2005_06
特許番号
US06903097B2

反応ノート

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