6-Chloropyridazin-3-ol → 6-Chloro-2-methyl-2,3-dihydropyridazin-3-one

HRID 2045997Notes

Reaction equation

HRID 2045997 reaction equation
[CH3:1][C:2]([CH3:36])([CH2:5][C@@:6]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[O:11][C:10](=[O:12])[N:9]([C@H:13]([C:15]2[CH:20]=[CH:19][C:18](B3OC(C)(C)C(C)(C)O3)=[CH:17][CH:16]=2)[CH3:14])[CH2:8][CH2:7]1)[C:3]#[N:4].[Cl:37][C:38]1[CH:39]=[CH:40][C:41](=[O:45])[N:42]([CH3:44])[N:43]=1.ClC1C=CC(=O)NN=1>>[CH3:1][C:2]([CH3:36])([CH2:5][C@@:6]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[O:11][C:10](=[O:12])[N:9]([C@H:13]([C:15]2[CH:20]=[CH:19][C:18]([C:38]3[CH:39]=[CH:40][C:41](=[O:45])[N:42]([CH3:44])[N:43]=3)=[CH:17][CH:16]=2)[CH3:14])[CH2:8][CH2:7]1)[C:3]#[N:4].[Cl:37][C:38]1[CH:39]=[CH:40][C:41](=[O:45])[N:42]([CH3:44])[N:43]=1

Participants

5

Reactant 3

HCID 2528286-Chloropyridazin-3-olHCID 27836076-Chloro-2-methyl-2,3-dihydropyridazin-3-oneHCID 596356852,2-dimethyl-3-((R)-2-oxo-6-phenyl-3-((S)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)-1,3-oxazinan-6-yl)propanenitrile

Product 2

HCID 27836076-Chloro-2-methyl-2,3-dihydropyridazin-3-oneHCID 44512035HCID 44512035, compound

Procedure

The title compound was prepared from 2,2-dimethyl-3-((R)-2-oxo-6-phenyl-3-((S)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)-1,3-oxazinan-6-yl)propanenitrile and 6-chloro-2-methylpyridazin-3(2H)-one following a procedure analogous to that described in Example 1 Step 3. 6-chloro-2-methylpyridazin-3(2H)-one was prepared from 6-chloropyridazin-3-(2H)-one following a procedure analogous to that described in Example 1 Step 2. LC-MS Method 2 tR=1.138 min, m/z=471.3; 1H NMR (CDCl3) 1.28 (s, 3H), 1.41 (s, 3H), 1.49 (m, 3H), 2.1 (s, 2H), 2.2 (m, 1H), 2.42 (m, 2H), 2.85 (m, 1H), 3.78 (s, 3H), 6.92 (m, 3H), 7.31 (m, 5H), 7.43 (d, 2H), 7.50 (d, 1H), 7.35 (m, 8H)

Sources & evidence

ORD record
ord-7f45304120a6473fb821bce2aee40565
Source dataset
uspto-grants-2013_11
Patent number
US08592410B2

Reaction notes

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