3-Chloro-6-methylpyridazine → (R)-6-(2-(5-methyl-1,3,4-oxadiazol-2-yl)ethyl)-3-((S)-1-(4-(6-methylpyridazin-3-yl)phenyl)ethyl)-6-phenyl-1,3-oxazinan-2-one

HRID 1046076Notes

Reaction equation

[CH3:1][C:2]1[O:6][C:5]([CH2:7][CH2:8][C@@:9]2([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[O:14][C:13](=[O:15])[N:12]([C@H:16]([C:18]3[CH:23]=[CH:22][C:21](B4OC(C)(C)C(C)(C)O4)=[CH:20][CH:19]=3)[CH3:17])[CH2:11][CH2:10]2)=[N:4][N:3]=1.Cl[C:40]1[N:41]=[N:42][C:43]([CH3:46])=[CH:44][CH:45]=1>>[CH3:1][C:2]1[O:6][C:5]([CH2:7][CH2:8][C@@:9]2([C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)[O:14][C:13](=[O:15])[N:12]([C@H:16]([C:18]3[CH:19]=[CH:20][C:21]([C:40]4[N:41]=[N:42][C:43]([CH3:46])=[CH:44][CH:45]=4)=[CH:22][CH:23]=3)[CH3:17])[CH2:11][CH2:10]2)=[N:4][N:3]=1

Participants

Reactant 2

HCID 2272543-Chloro-6-methylpyridazine

HCID 59635664HCID 59635664, compound

Product 1

HCID 58485298(R)-6-(2-(5-methyl-1,3,4-oxadiazol-2-yl)ethyl)-3-((S)-1-(4-(6-methylpyridazin-3-yl)phenyl)ethyl)-6-phenyl-1,3-oxazinan-2-one

Procedure

(R)-6-(2-(5-methyl-1,3,4-oxadiazol-2-yl)ethyl)-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 3-chloro-6-methylpyridazine were reacted following a procedure analogous to that described in Example 1 Step 2 to afford (R)-6-(2-(5-methyl-1,3,4-oxadiazol-2-yl)ethyl)-3-((S)-1-(4-(6-methylpyridazin-3-yl)phenyl)ethyl)-6-phenyl-1,3-oxazinan-2-one. LC-MS Method 2 tR=0.984 min, m/z=499.1; 1H NMR (CD3OD) 1.50 (m, 3H), 2.25 (m, 2H), 2.42 (m, 1H), 2.35 (s, 3H), 2.38 (m, 1H), 2.42 (m, 1H), 2.49-2.55 (m, 1H), 2.65 (s, 3H), 2.90 (m, 1H), 3.05 (m, 1H), 5.52 (m, 1H), 7.07 (m, 2H), 7.25 (m, 3H), 7.32 (m, 2H), 7.69-7.76 (m, 3H), 8.06 (m, 1H)

Sources & evidence

ORD record: ord-2d776f8f05134219a0568b31688d115e
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08569292B2

Reaction notes

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