(Dimethyl sulfide)trihydroboron → (+/-)-3-amino-4-chloro-5-((4aR,8aR)-hexahydro-1H-pyrido[3,4-b][1,4]oxazin-6(7H)-yl)benzonitrile

HRID 921731ノート

反応式

HRID 921731 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([N:11]2[CH2:20][CH2:19][C@@H:18]3[C@H:13]([O:14][CH2:15][C:16](=O)[NH:17]3)[CH2:12]2)[C:9]=1[Cl:10])[C:5]#[N:6].B.CSC>O1CCCC1>[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([N:11]2[CH2:20][CH2:19][C@@H:18]3[C@H:13]([O:14][CH2:15][CH2:16][NH:17]3)[CH2:12]2)[C:9]=1[Cl:10])[C:5]#[N:6]

参加物

4

反応物 2

HCID 12423031(Dimethyl sulfide)trihydroboronHCID 86708613(+/-)-3-amino-4-chloro-5-((4aR,8aR)-2-oxohexahydro-1H-pyrido[3,4-b][1,4]oxazin-6(7H)-yl)benzonitrile

生成物 1

HCID 86708614(+/-)-3-amino-4-chloro-5-((4aR,8aR)-hexahydro-1H-pyrido[3,4-b][1,4]oxazin-6(7H)-yl)benzonitrile収率 94.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
90 °C

実験手順

(+/−)-3-amino-4-chloro-5-((4aR,8aR)-2-oxohexahydro-1H-pyrido[3,4-b][1,4]oxazin-6(7H)-yl)benzonitrile (Example 370B) (144 mg, 0.469 mmol) was dissolved in Tetrahydrofuran (10 ml) in a 20 ml scintillation vial. Borane-methyl sulfide complex (2 M in THF) (0.493 ml, 0.986 mmol) was added, the vial was capped and the reaction mixture heated to 90° C. for 3 hours. The reaction mixture was partitioned between EtOAc and aq. NH4Cl solution. The organic layer was washed with brine, then dried over MgSO4, filtered and evaporated to dryness to give (+/−)-3-amino-4-chloro-5-((4aR,8aR)-hexahydro-1H-pyrido[3,4-b][1,4]oxazin-6(7H)-yl)benzonitrile (129.5 mg)

後処理

  1. customthe vial was capped
  2. customThe reaction mixture was partitioned between EtOAc and aq. NH4Cl solution
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated to dryness

出典と根拠

ORDレコード
ord-42d6419985164b84b188845239ac935d
出典データセット
uspto-grants-2016_03
特許番号
US09273057B2

反応ノート

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