N-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indoline-1-carboxamide → 5-(3-amino-6-(4-(N-cyclopropyl-N-methylsulfamoyl)phenyl)pyrazin-2-yl)-N-methylindoline-1-carboxamide

HRID 2091605Notes

Reaction equation

HRID 2091605 reaction equation
[CH3:1][NH:2][C:3]([N:5]1[C:13]2[C:8](=[CH:9][C:10](B3OC(C)(C)C(C)(C)O3)=[CH:11][CH:12]=2)[CH2:7][CH2:6]1)=[O:4].[NH2:23][C:24]1[N:25]=[CH:26][C:27]([C:31]2[CH:36]=[CH:35][C:34]([S:37]([N:40]([CH:42]3[CH2:44][CH2:43]3)[CH3:41])(=[O:39])=[O:38])=[CH:33][CH:32]=2)=[N:28][C:29]=1Br>>[NH2:23][C:24]1[C:29]([C:10]2[CH:9]=[C:8]3[C:13](=[CH:12][CH:11]=2)[N:5]([C:3]([NH:2][CH3:1])=[O:4])[CH2:6][CH2:7]3)=[N:28][C:27]([C:31]2[CH:36]=[CH:35][C:34]([S:37](=[O:39])(=[O:38])[N:40]([CH:42]3[CH2:43][CH2:44]3)[CH3:41])=[CH:33][CH:32]=2)=[CH:26][N:25]=1

Participants

3

Reactant 2

HCID 70654696N-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indoline-1-carboxamideHCID 866702144-(5-amino-6-bromopyrazin-2-yl)-N-cyclopropyl-N-methylbenzenesulfonamide

Product 1

HCID 601966625-(3-amino-6-(4-(N-cyclopropyl-N-methylsulfamoyl)phenyl)pyrazin-2-yl)-N-methylindoline-1-carboxamideYield 28.1%

Procedure

Method C was applied to N-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indoline-1-carboxamide (85 mg, 0.28 mmol) and 4-(5-amino-6-bromopyrazin-2-yl)-N-cyclopropyl-N-methylbenzenesulfonamide (100 mg, 0.26 mmol). The organic layer was decanted then triturated with Et2O to provide 5-(3-amino-6-(4-(N-cyclopropyl-N-methylsulfamoyl)phenyl)pyrazin-2-yl)-N-methylindoline-1-carboxamide as a yellow solid (35 mg, 28% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.58-8.66 (m, 1H), 8.20-8.31 (m, 1H), 7.92-7.99 (m, 1H), 7.79-7.88 (m, 2H), 7.47-7.64 (m, 2H), 6.61-6.71 (m, 1H), 6.60-6.65 (m, 1H), 6.58-6.71 (m, 2H), 6.42-6.49 (m, 2H), 3.88-3.98 (m, 2H), 3.13-3.25 (m, 2H), 2.68 (s, 3H), 2.08 (s, 3H), 1.79-1.88 (m, 1H), 0.62-0.81 (m, 4H); MS (EI) m/z=479.1[M+1]+.

Workup

  1. customThe organic layer was decanted
  2. customthen triturated with Et2O

Sources & evidence

ORD record
ord-6acb4c26c09b4bb4b6b2869df57a1d82
Source dataset
uspto-grants-2013_05
Patent number
US08440652B2

Reaction notes

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