Ethanesulfonyl chloride → US10023592, Example 213

HRID 575686Notes

Reaction equation

HRID 575686 reaction equation
Cl[C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][N:3]=1.[CH2:9]([S:11](Cl)(=[O:13])=[O:12])[CH3:10].[CH3:15][N:16]1[CH:25]=[C:24](B2OC(C)(C)C(C)(C)O2)[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([C:35]3[CH:36]=[N:37][N:38]([CH3:40])[CH:39]=3)[CH:22]=2)[C:17]1=[O:41]>>[CH3:15][N:16]1[CH:25]=[C:24]([C:2]2[CH:7]=[C:6]([NH:8][S:11]([CH2:9][CH3:10])(=[O:13])=[O:12])[CH:5]=[CH:4][N:3]=2)[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([C:35]3[CH:36]=[N:37][N:38]([CH3:40])[CH:39]=3)[CH:22]=2)[C:17]1=[O:41]

Participants

4

Reactant 3

HCID 11667Ethanesulfonyl chlorideHCID 844322-Chloropyridin-4-amineHCID 1237513492-Methyl-6-(1-methylpyrazol-4-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoquinolin-1-one

Product 1

HCID 118022049US10023592, Example 213

Procedure

The title compound was prepared after 2-chloropyridin-4-amine was sulfonylated with ethanesulfonyl chloride and the resulting product was coupled to the title compound of Example 46, step 2. 1H NMR (CDCl3, 400 MHz) δ 10.65 (brs, 1H), 8.56 (s, 1H), 8.29 (d, J=8.4 Hz, 1H), 8.22 (s, 1H), 8.01-7.73 (m, 4H), 7.37 (s, 1H), 7.18 (s, 1H), 3.87 (s, 3H), 3.59 (s, 3H), 1.25 (t, J=7.2 Hz, 3H). LCMS: 424.0 (M+1)+

Sources & evidence

ORD record
ord-4e18b122d6874cb3a7524f04cfc00d9f
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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