HCID 90253497, compound → HCID 118621157, compound

HRID 1478776Notes

Reaction equation

HRID 1478776 reaction equation
[O:1]1[CH2:5][CH2:4][CH2:3][C@H:2]1[C@@H:6]1[O:14][CH2:13][C:9]2=[N:10][O:11][CH2:12][C@@H:8]2[CH2:7]1.[F:15][C:16]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=1C12COC([C@@H]3C[C@H]3C)CC1CON2>>[F:15][C:16]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=1[C@:9]12[CH2:13][O:14][C@@H:6]([C@@H:2]3[CH2:3][CH2:4][CH2:5][O:1]3)[CH2:7][C@H:8]1[CH2:12][O:11][NH:10]2

Participants

3

Reactant 2

HCID 90253497HCID 90253497, compoundHCID 90253540HCID 90253540, compound

Product 1

HCID 118621157HCID 118621157, compound

Procedure

(3aR,5R)-5-[(2S)-Tetrahydrofuran-2-yl]-3,3a,4,5-tetrahydro-7H-pyrano[3,4-c][1,2]oxazole (C99) was converted to the product using the method described for the synthesis of 7a-(2,4-difluorophenyl)-5-[(1R,2R)-2-methylcyclopropyl]hexahydro-1H-pyrano[3,4-c][1,2]oxazole (C86) in Example 20. Yield: 1.4 g, 4.5 mmol, 36%. LCMS m/z 312.1 [M+H+]. 1H NMR (400 MHz, CDCl3) δ 7.89-7.95 (m, 1H), 6.87-6.91 (m, 1H), 6.77-6.83 (m, 1H), 6.29 (s, 1H), 4.10 (dd, J=12.5, 1.5 Hz, 1H), 3.72-3.92 (m, 5H), 3.53-3.57 (m, 2H), 3.07 (dt, J=11.4, 5.6 Hz, 1H), 1.79-2.03 (m, 5H), 1.46-1.55 (m, 1H).

Sources & evidence

ORD record
ord-546e349ed4054c0790fc37878b8abfff
Source dataset
uspto-grants-2016_08
Patent number
US09403846B2

Reaction notes

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