7-Bromo[1,2,4]triazolo[1,5-a]pyridine → HCID 66745486, compound

HRID 1907344Notes

Reaction equation

HRID 1907344 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:42]=[CH:41][N:40]2[N:43]=[CH:44][N:45]=[C:39]2[CH:38]=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:42]=[CH:41][N:40]4[N:43]=[CH:44][N:45]=[C:39]4[CH:38]=3)=[CH:17][CH:18]=2)[CH3:12])[CH2:6][CH2:5]1

Participants

3

Reactant 2

HCID 378185337-Bromo[1,2,4]triazolo[1,5-a]pyridineHCID 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

Product 1

HCID 66745486HCID 66745486, compoundYield 68%

Procedure

The title compound was prepared from (S)-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 7-bromo-[1,2,4]triazolo[1,5-a]pyridine following a procedure analogous to that described in EXAMPLE 7. Yield: 68% of theory; Mass spectrum (ESI+): m/z=471 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ 0.82 (s, 3H), 1.19 (s, 3H), 1.49 (d, J=7.1 Hz, 3H), 2.03 (s, 2H), 2.14-2.23 (m, 1H), 2.39-ca. 2.55 (m, 2H) superimposed on DMSO-d5, 3.01-3.09 (m, 1H), 4.23 (s, 1H), 5.46 (q, J=7.1 Hz, 1H), 7.02 (dm, J=8.3 Hz, 2H), 7.27-7.41 (m, 5H), 7.46 (dm, J=7.2, 1.8 Hz, 1H), 7.62 (dm, J=8.3 Hz, 2H), 8.06 (hardly resolved d, 1H), 8.52 (s, 1H), 8.98 (d, J=7.2 Hz, 1H).

Sources & evidence

ORD record
ord-1d943de24e6e4db3a9411155de32281e
Source dataset
uspto-grants-2013_12
Patent number
US08598163B2

Reaction notes

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