(4aS,7aR)-Hexahydro-cyclopenta[d][1,3]oxazin-2-one → (4aS,7aR)-1-[5-(3-Fluorophenylethynyl)-pyridin-2-yl]-hexahydro-cyclopenta[d][1,3]oxazin-2-one

HRID 1507135Notes

Reaction equation

HRID 1507135 reaction equation
[NH:1]1[C@@H:6]2[CH2:7][CH2:8][CH2:9][C@@H:5]2[CH2:4][O:3][C:2]1=[O:10].F[C:12]1[CH:17]=[CH:16][C:15]([C:18]#[C:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=2)=[CH:14][N:13]=1>>[F:26][C:22]1[CH:21]=[C:20]([C:19]#[C:18][C:15]2[CH:16]=[CH:17][C:12]([N:1]3[C@@H:6]4[CH2:7][CH2:8][CH2:9][C@@H:5]4[CH2:4][O:3][C:2]3=[O:10])=[N:13][CH:14]=2)[CH:25]=[CH:24][CH:23]=1

Participants

3

Reactant 2

HCID 117871704(4aS,7aR)-Hexahydro-cyclopenta[d][1,3]oxazin-2-oneHCID 1178721812-Fluoro-5-((3-fluorophenyl)ethynyl)pyridine

Product 1

HCID 73443119(4aS,7aR)-1-[5-(3-Fluorophenylethynyl)-pyridin-2-yl]-hexahydro-cyclopenta[d][1,3]oxazin-2-oneYield 31%

Procedure

The title compound was prepared in accordance with the general method of Example 1, step 4 using (4aS,7aR)-hexahydro-cyclopenta[d]-[1,3]oxazin-2-one (66 mg, 0.47 mmol) (Example 1, step 2) and 2-fluoro-5-((3-fluorophenyl)ethynyl)pyridine (100 mg, 0.47 mmol) to yield 48 mg (31%) of the title compound as a light yellow amorphous solid; MS: m/e=337.3 (M+H+).

Sources & evidence

ORD record
ord-684134681ab34f4caea59c6ed9c7aa15
Source dataset
uspto-grants-2015_12
Patent number
US09221802B2

Reaction notes

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