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

HRID 921731노트

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HRID 921731 반응식
[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]

참가 물질

4

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
90 °C

실험 절차

(+/−)-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)

후처리

  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

출처 및 근거

ORD 기록
ord-42d6419985164b84b188845239ac935d
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09273057B2

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