6-bromo-2-methyl-[1,2,4]triazolo[1,5-a]pyridine → HCID 46865564, compound

HRID 1907342Notes

Reaction equation

HRID 1907342 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]([CH3:46])[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]([CH3:46])[N:45]=4)[CH:42]=3)=[CH:17][CH:18]=2)[CH3:12])[CH2:6][CH2:5]1

Participants

3

Reactant 2

HCID 6111916-bromo-2-methyl-[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 46865564HCID 46865564, compound

Procedure

The title compound was prepared from (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 and 6-bromo-2-methyl-[1,2,4]triazolo[1,5-a]pyridine following a procedure analogous to that described in Example 3. LC-MS Method 2 tR=1.27 min, 507, 485; 1H NMR (CD3OD) δ 0.97 (s, 3H), 1.29 (s, 3H), 1.58 (d, 3H), 2.18 (s, 2H), 2.27 (m, 1H), 2.51 (m, 2H), 2.63 (s, 3H), 3.10 (m, 1H), 5.62 (q, 1H), 7.13 (d, 2H), 7.30-7.40 (5H), 7.52 (d, 2H), 7.82 (d, 1H), 8.05 (d, 1H), 8.96 (s, 1H).

Sources & evidence

ORD record
ord-38216ad1fbb1469786154c751e6e6ecd
Source dataset
uspto-grants-2013_12
Patent number
US08598163B2

Reaction notes

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