HCID 58304243, compound → HCID 58304200, compound

HRID 1941784Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[C@:11]1([CH3:20])[C:16]([F:18])([F:17])[CH2:15][O:14][C:13]([NH2:19])=[N:12]1>O1CCCC1.[Ni]>[NH2:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([C@:11]2([CH3:20])[C:16]([F:17])([F:18])[CH2:15][O:14][C:13]([NH2:19])=[N:12]2)[CH:4]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Under an inert atmosphere of argon a solution of (R)-4-(2-chloro-5-nitro-phenyl)-5,5-difluoro-4-methyl-5,6-dihydro-4H-[1,3]oxazin-2-ylamine (intermediate X-3) (50 mg, 0.16 mmol) in tetrahydrofurane (1 ml) was treated at 0° C. with Raney nickel (50% in water, 0.07 ml). The mixture was stirred under hydrogen atmosphere at 0° C. for 15 minutes. The catalyst was filtered off and the filtrate was evaporated at reduced pressure to give the (R)-4-(5-amino-2-chloro-phenyl)-5,5-difluoro-4-methyl-5,6-dihydro-4H-[1,3]oxazin-2-ylamine (42 mg, 93% of theory) as a yellow oil which was used without further purification. MS (ISP): m/z=276.1 [M+H]+.

Workup

filtrationThe catalyst was filtered off
customthe filtrate was evaporated at reduced pressure

Sources & evidence

ORD record: ord-4d295982e53c4ac8962587880be5f09b
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08389513B2

Reaction notes

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