Cyclopropanecarbonyl chloride → US10023592, Example 220

HRID 575691Notes

Reaction equation

HRID 575691 reaction equation
Br[C:2]1[CH:8]=[C:7]([S:9]([CH3:12])(=[O:11])=[O:10])[CH:6]=[CH:5][C:3]=1[NH2:4].[CH3:13][N:14]1[CH:23]=[C:22](B2OC(C)(C)C(C)(C)O2)[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]1=[O:33].[CH:34]1([C:37](Cl)=[O:38])[CH2:36][CH2:35]1.C(N(C(C)C)CC)(C)C>C1COCC1>[CH3:13][N:14]1[CH:23]=[C:22]([C:2]2[CH:8]=[C:7]([S:9]([CH3:12])(=[O:11])=[O:10])[CH:6]=[CH:5][C:3]=2[NH:4][C:37]([CH:34]2[CH2:36][CH2:35]2)=[O:38])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]1=[O:33]

Participants

6

Reactant 4

HCID 77637Cyclopropanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 201344022-Bromo-4-methanesulfonylanilineHCID 1238094992-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoquinolin-1(2H)-one

Product 1

HCID 118021459US10023592, Example 220

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-bromo-4-methanesulfonylaniline was coupled to the title compound of Example 89, step 1 in a manner similar to Example 89, step 2. The resulting product was reacted with cyclopropanecarbonyl chloride using diisopropylethylamine in THF to prepare the title compound. 1H NMR (CDCl3, 400 MHz) δ 9.38 (s, 1H), 8.34 (d, J=8.0 Hz, 1H), 8.23 (d, J=8.8 Hz, 1H), 7.96 (d, J=8.8 Hz, 1H), 7.83 (s, 1H), 7.53-7.64 (m, 3H), 6.94 (d, J=8.0 Hz, 1H), 3.59 (s, 3H), 3.25 (m, 3H), 1.64 (brs, 1H), 0.52-0.75 (m, 4H). LCMS: 397.0 (M+1)+

Sources & evidence

ORD record
ord-b70fc8aeb84e4698be225e44392f27ea
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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