(S)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-3-((S)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)-1,3-oxazinan-2-one → HCID 66746339, compound

HRID 1907345Notes

Reaction equation

[OH:1][C:2]([CH3:35])([CH3:34])[CH2:3][C@@:4]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]([C:13]2[CH:18]=[CH:17][C:16](B3OC(C)(C)C(C)(C)O3)=[CH:15][CH:14]=2)[CH3:12])[CH2:6][CH2:5]1.Br[C:37]1[CH:38]=[CH:39][C:40]2[N:41]([N:43]=[C:44]([O:46][CH3:47])[N:45]=2)[CH:42]=1>>[OH:1][C:2]([CH3:34])([CH3:35])[CH2:3][C@@:4]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]([C:13]2[CH:14]=[CH:15][C:16]([C:37]3[CH:38]=[CH:39][C:40]4[N:41]([N:43]=[C:44]([O:46][CH3:47])[N:45]=4)[CH:42]=3)=[CH:17][CH:18]=2)[CH3:12])[CH2:6][CH2:5]1

Participants

Reactant 2

HCID 59532385(S)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-3-((S)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)-1,3-oxazinan-2-one

HCID 66745550HCID 66745550, compound

Product 1

HCID 66746339HCID 66746339, compoundYield 66%

Procedure

The title compound was prepared from (5)-6-(2-hydroxy-2-methyl-propyl)-6-phenyl-3-{(S)-1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-ethyl}-[1,3]oxazinan-2-one and 6-bromo-2-methoxy-[1,2,4]triazolo[1,5-a]pyridine following a procedure analogous to that described in EXAMPLE 7. Yield: 66% of theory; Mass spectrum (ESI+): m/z=501 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ 0.81 (s, 3H), 1.19 (s, 3H), 1.48 (d, J=7.0 Hz, 3H), 2.03 (s, 2H), 2.13-2.22 (m, 1H), 2.38-ca. 2.53 (m, 2H) superimposed on DMSO-d5, 3.00-3.07 (m, 1H), 4.04 (s, 3H), 4.23 (s, 1H), 5.44 (q, J=7.0 Hz, 1H), 6.98 (d, J=8.2 Hz, 2H), 7.27-7.40 (m, 5H), 7.51 (dm, J=8.2 Hz, 2H), 7.67 (d, J=9.2 Hz, 1H), 7.82 (dd, J=9.2, 1.8 Hz, 1H), 9.05 (hardly resolved d, 1H).

Sources & evidence

ORD record: ord-9cca87f488994cd9a491eec19b00d370
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598163B2

Reaction notes

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