4-methoxy-N-(2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-indole-2-carboxamide → HCID 178487944, compound

HRID 245734Notes

Reaction equation

HRID 245734 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[C:6]([C:12]([NH:14][C:15]1[CH:20]=[CH:19][C:18](B3OC(C)(C)C(C)(C)O3)=[CH:17][C:16]=1[O:30][CH3:31])=[O:13])[NH:7]2.Br[C:33]1[N:34]=[C:35]([C@H:43]2[CH2:48][CH2:47][C@H:46]([N:49]3[CH2:54][CH2:53][N:52]([CH3:55])[CH2:51][CH2:50]3)[CH2:45][CH2:44]2)[N:36]2[CH:41]=[CH:40][N:39]=[C:38]([CH3:42])[C:37]=12>>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[C:6]([C:12]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([C:33]3[N:34]=[C:35]([C@H:43]4[CH2:48][CH2:47][C@H:46]([N:49]5[CH2:54][CH2:53][N:52]([CH3:55])[CH2:51][CH2:50]5)[CH2:45][CH2:44]4)[N:36]4[CH:41]=[CH:40][N:39]=[C:38]([CH3:42])[C:37]=34)=[CH:17][C:16]=1[O:30][CH3:31])=[O:13])[NH:7]2

Participants

3

Reactant 2

HCID 673640964-methoxy-N-(2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-indole-2-carboxamideHCID 178432912HCID 178432912, compound

Product 1

HCID 178487944HCID 178487944, compoundYield 23.9%

Procedure

Reaction of 4-methoxy-N-(2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-indole-2-carboxamide (32 mg) and 1-bromo-8-methyl-3-((trans)-4-(4-methylpiperazin-1-yl)cyclohexyl)imidazo[1,5-a]pyrazine (30 mg) according to the procedure described in example 4 step 4c and purification by column chromatography (silica gel; dichloromethane with gradient 0 to 20% of methanol) gave 4-methoxy-N-(2-methoxy-4-(8-methyl-3-((trans)-4-(4-methylpiperazin-1-yl)cyclohexyl)imidazo[1,5-a]pyrazin-1-yl)phenyl)-1H-indole-2-carboxamide (11 mg)

Workup

  1. customdescribed in example 4 step 4c and purification by column chromatography (silica gel; dichloromethane with gradient 0 to 20% of methanol)

Sources & evidence

ORD record
ord-287a529f20b148688e307967e9543b09
Source dataset
uspto-grants-2014_02
Patent number
US08658794B2

Reaction notes

Loading…