Cesium carbonate → 3-[(2,3-Dimethyl-4-oxo-3,4-dihydro-2H-1,3-benzoxazin-7-yl)oxy]-5-{[(1S)-2-hydroxy-1-methylethyl]oxy}-N-(3-methyl-1,2,4-thiadiazol-5-yl)benzamide

HRID 548764ノート

反応式

HRID 548764 の反応式
C(=O)([O-])[O-].[Cs+].[Cs+].[OH:7][C:8]1[CH:9]=[C:10]([CH:20]=[C:21]([O:23][C@@H:24]([CH3:27])[CH2:25][OH:26])[CH:22]=1)[C:11]([NH:13][C:14]1[S:18][N:17]=[C:16]([CH3:19])[N:15]=1)=[O:12].F[C:29]1[CH:41]=[CH:40][C:32]2[C:33](=[O:39])[N:34]([CH3:38])[CH2:35][CH2:36][O:37][C:31]=2[CH:30]=1>CC(N(C)C)=O>[CH3:35][CH:36]1[N:34]([CH3:38])[C:33](=[O:39])[C:32]2[CH:40]=[CH:41][C:29]([O:7][C:8]3[CH:9]=[C:10]([CH:20]=[C:21]([O:23][C@@H:24]([CH3:27])[CH2:25][OH:26])[CH:22]=3)[C:11]([NH:13][C:14]3[S:18][N:17]=[C:16]([CH3:19])[N:15]=3)=[O:12])=[CH:30][C:31]=2[O:37]1

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 576631608-fluoro-4-methyl-3,4-dihydro-1,4-benzoxazepin-5(2H)-oneHCID 591271603-hydroxy-5-{[(1S)-2-hydroxy-1-methylethyl]oxy}-N-(3-methyl-1,2,4-thiadiazol-5-yl)benzamide

生成物 1

HCID 159500393-[(2,3-Dimethyl-4-oxo-3,4-dihydro-2H-1,3-benzoxazin-7-yl)oxy]-5-{[(1S)-2-hydroxy-1-methylethyl]oxy}-N-(3-methyl-1,2,4-thiadiazol-5-yl)benzamide収率 64.4%

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

反応条件

温度
160 °C

実験手順

Cesium carbonate (489 mg, 1.5 mmol) was added to a solution of 3-hydroxy-5-{[(1S)-2-hydroxy-1-methylethyl]oxy}-N-(3-methyl-1,2,4-thiadiazol-5-yl)benzamide (155 mg, 0.5 mmol) and 8-fluoro-4-methyl-3,4-dihydro-1,4-benzoxazepin-5(2H)-one (117 mg, 0.6 mmol) in DMA (5 mL) and the stirred mixture heated at 160° C. in a microwave reactor for 8 hours. The mixture was cooled to RT and pressure, the DMA removed in vacuo, and the residue partitioned between water (25 mL) and ethyl acetate (30 mL). The mixture was adjusted to pH 2, the organic layer washed with brine, dried (MgSO4) and evaporated in vacuo to a residue which was chromatographed on silica, eluting with ethyl acetate, to give desired compound (156 mg). 1H NMR δ (CDCl3): 1.3 (d, 3H), 1.5 (d, 2H), 2.4 (s, 3H), 3.0 (s, 3H), 3.7 (d, 2H), 4.5 (m, 1H), 5.35 (q, 1H), 6.4 (s, 1H), 6.6 (d, 1H), 6.75 (s, 1H), 7.15 (s, 1H), 7.2 (s, 1H), 7.8 (d, 1H); m/z 485 (M+H)+

後処理

  1. temperatureThe mixture was cooled to RT
  2. custompressure, the DMA removed in vacuo
  3. customthe residue partitioned between water (25 mL) and ethyl acetate (30 mL)
  4. washthe organic layer washed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated in vacuo to a residue which
  7. customwas chromatographed on silica
  8. washeluting with ethyl acetate

出典と根拠

ORDレコード
ord-3d9f88d39d584b38b3dd0aa33e49d68b
出典データセット
uspto-grants-2011_05
特許番号
US07943607B2

反応ノート

読み込み中…