3-Chloro-6-methylpyridazine → HCID 49793199, compound

HRID 2368051Notes

Reaction equation

[CH:1]1([C@@H:4]([C:23]2[CH:28]=[CH:27][C:26](B3OC(C)(C)C(C)(C)O3)=[CH:25][CH:24]=2)[N:5]2[CH2:10][CH2:9][C@:8]([CH2:17][C:18]([OH:21])([CH3:20])[CH3:19])([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[O:7][C:6]2=[O:22])[CH2:3][CH2:2]1.BrC1C=CC([C@H](C2CC2)N2CC[C@](CC(O)(C)C)(C3C=CC=CC=3)OC2=O)=CC=1.Cl[C:68]1[N:69]=[N:70][C:71]([CH3:74])=[CH:72][CH:73]=1>>[CH:1]1([C@@H:4]([C:23]2[CH:28]=[CH:27][C:26]([C:68]3[N:69]=[N:70][C:71]([CH3:74])=[CH:72][CH:73]=3)=[CH:25][CH:24]=2)[N:5]2[CH2:10][CH2:9][C@:8]([CH2:17][C:18]([OH:21])([CH3:20])[CH3:19])([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[O:7][C:6]2=[O:22])[CH2:2][CH2:3]1

Participants

Reactant 3

HCID 2272543-Chloro-6-methylpyridazine

HCID 49838825HCID 49838825, compound

HCID 68759713HCID 68759713, compound

Product 1

HCID 49793199HCID 49793199, compound

Procedure

The title compound was prepared from 3-{(S)-cyclopropyl-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]methyl}-(S)-6-(2-hydroxy-2-methyl-propyl)-6-phenyl-[1,3]oxazinan-2-one {prepared in analogy to the intermediate in Example 3 from 3-[(S)-(4-bromo-phenyl)-cyclopropyl-methyl]-(S)-6-(2-hydroxy-2-methyl-propyl)-6-phenyl-[1,3]oxazinan-2-one} and 3-chloro-6-methyl-pyridazine following a procedure analogous to that described in Example 3. LC-MS (Method 1): tR=3.39 min; Mass spectrum (ESI+): m/z=472 [M+H]+.

Sources & evidence

ORD record: ord-04ff98ed88f849f4a9a6fbd89fe1b1e5
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08703765B2

Reaction notes

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