Sodium hydride → tert-butyl N-methyl-N-(4-[7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(12),2(6),8,10-tetraen-12-yloxy]cyclohexyl)carbamate

HRID 2369432

反応式

HRID 2369432 の反応式
[OH:1][CH:2]1[CH2:7][CH2:6][CH:5]([N:8]([CH3:16])[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:4][CH2:3]1.[H-].[Na+].Cl[C:20]1[N:21]=[CH:22][N:23]=[C:24]2[C:31]=1[C:30]1[CH2:29][CH2:28][CH2:27][C:26]=1[S:25]2>C1COCC1>[CH3:16][N:8]([CH:5]1[CH2:6][CH2:7][CH:2]([O:1][C:20]2[N:21]=[CH:22][N:23]=[C:24]3[C:31]=2[C:30]2[CH2:29][CH2:28][CH2:27][C:26]=2[S:25]3)[CH2:3][CH2:4]1)[C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:13])[CH3:14]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 78981712-Chloro-7-thia-9,11-diazatricyclo(6.4.0.0,2,6)dodeca-1(12),2(6),8,10-tetraeneHCID 219251474-(N-Boc-N-methylamino)cyclohexanol

生成物 1

HCID 68110120tert-butyl N-methyl-N-(4-[7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(12),2(6),8,10-tetraen-12-yloxy]cyclohexyl)carbamate収率 74.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Into a 50-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of tert-butyl N-(4-hydroxycyclohexyl)-N-methylcarbamate (447 mg, 1.95 mmol, 1.30 equiv) in anhydrous THF (30 mL), then sodium hydride (300 mg, 7.50 mmol, 5.00 equiv, 60% dispersion in mineral oil) was added and stirring for 20 min at room temperature under nitrogen. Then 12-chloro-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(12),2(6),8,10-tetraene (316 mg, 1.50 mmol, 1.00 equiv) was added and stirred for 6 h at ambient temperature. The reaction mixture was quenched with NH4Cl (sat.) at 0° C., diluted with brine, extracted with EtOAc. The organic layer was washed with brine and dried over anhydrous sodium sulfate. After filtration and concentration, the residue was purified by a silica gel column with EA/PE (1:10-1:4) to provide tert-butyl N-methyl-N-(4-[7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(12),2(6),8,10-tetraen-12-yloxy]cyclohexyl)carbamate (450 mg, 74%) as a white solid. MS: (ES, m/z): 404 [M+H]+.

後処理

  1. customInto a 50-mL 3-necked round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. stirringstirred for 6 h at ambient temperature
  4. customThe reaction mixture was quenched with NH4Cl (sat.) at 0° C.
  5. additiondiluted with brine
  6. extractionextracted with EtOAc
  7. washThe organic layer was washed with brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationAfter filtration and concentration
  10. customthe residue was purified by a silica gel column with EA/PE (1:10-1:4)

出典と根拠

ORDレコード
ord-41bd81169c424de48f0457dae4362040
出典データセット
uspto-grants-2014_04
特許番号
US08703941B2

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