Ethyl Acetate → 5-chloro-N-(((3S,3aS)-1-oxo-7-(2-t-butylaminosulfonylphenyl)-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-3-yl)methyl)thiophene-2-carboxamide

HRID 1050222ノート

反応式

HRID 1050222 の反応式
[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH2:10][C@H:11]2[C@H:19]3[N:14]([C:15]4[CH:23]=[CH:22][C:21](B5OC(C)(C)C(C)(C)O5)=[CH:20][C:16]=4[O:17][CH2:18]3)[C:13](=[O:33])[O:12]2)=[O:8])=[CH:4][CH:3]=1.[C:34]([NH:38][S:39]([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=1Br)(=[O:41])=[O:40])([CH3:37])([CH3:36])[CH3:35].C(=O)([O-])[O-].[Cs+].[Cs+].CC(=O)OCC>O1CCOCC1.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH2:10][C@H:11]2[C@H:19]3[N:14]([C:15]4[CH:23]=[CH:22][C:21]([C:43]5[CH:44]=[CH:45][CH:46]=[CH:47][C:42]=5[S:39]([NH:38][C:34]([CH3:37])([CH3:36])[CH3:35])(=[O:40])=[O:41])=[CH:20][C:16]=4[O:17][CH2:18]3)[C:13](=[O:33])[O:12]2)=[O:8])=[CH:4][CH:3]=1

参加物

8

反応物 4

HCID 8857Ethyl Acetate2 回HCID 10796Cesium carbonateHCID 48250142-bromo-N-tert-butylbenzenesulfonamideHCID 1317360535-chloro-N-(((3S,3 aS)-1-oxo-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-3-yl)methyl)thiophene-2-carboxamide

生成物 1

HCID 1185196015-chloro-N-(((3S,3aS)-1-oxo-7-(2-t-butylaminosulfonylphenyl)-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-3-yl)methyl)thiophene-2-carboxamide収率 35.6%

試薬・触媒・溶媒 3

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

Compound 5-chloro-N-(((3S,3aS)-1-oxo-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-3-yl)methyl)thiophene-2-carboxamide (60 mg, 0.122 mmol) and N-t-butyl-o-bromobenzenesulfonamide (43 mg, 0.147 mmol) were dissolved in a mixed solvent of dioxane (5 ml) and water (0.5 ml). Cesium carbonate (80 mg, 0.245 mmol) was added, and tetrakis (triphenylphosphine) palladium (15 mg, 0.012 mmol) was added under the protection of Ar. The resulting mixture was allowed to react under agitation at 80° C. overnight. TLC (PE/EA=1/1) was employed to monitor the reaction. After the reaction completed, the mixture was filtered under reduced pressure, and the solvent was evaporated. Column chromatography (PE/EA=2/1) afforded off-white solid 25 mg, yield: 35.2%.

後処理

  1. customto react under agitation at 80° C. overnight
  2. customthe reaction
  3. filtrationthe mixture was filtered under reduced pressure
  4. customthe solvent was evaporated

出典と根拠

ORDレコード
ord-36c9b5179feb4e2f85e30ef9ee93d1e1
出典データセット
uspto-grants-2016_07
特許番号
US09382265B2

反応ノート

読み込み中…