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

HRID 1430909Notes

Reaction equation

[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]

Participants

Conditions

Temperature: 90 °C

Procedure

(+/−)-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)

Workup

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

Sources & evidence

ORD record: ord-a7992de8679a4d99b6b8b0f1c01f8fd5
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940736B2

Reaction notes

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