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 411216노트

반응식

HRID 411216 반응식
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]

참가 물질

6

반응물 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

생성물 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-dioxide수율 66%

시약·촉매·용매 2

HCID 8471Triethylamine촉매HCID 1140Toluene용매

실험 절차

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 (0.49g) 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) δ 1.52-1.86, 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.

후처리

  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)

출처 및 근거

ORD 기록
ord-02f387b5b38642878b11420e9e9c991a
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06559145B2

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